Potassium Phosphate, Tribasic → methyl 7-(morpholinosulfonyl)-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxylate

HRID 2410868노트

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HRID 2410868 반응식
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[CH:12]=[C:13]([C:33]([O:35][CH3:36])=[O:34])[C:14]2[NH:15][C:16]3[CH:17]=[C:18]([S:24]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)(=[O:26])=[O:25])[CH:19]=[CH:20][C:21]=3[C:22]=2[N:23]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>CC([O-])=O.CC([O-])=O.[Pd+2]>[O:30]1[CH2:31][CH2:32][N:27]([S:24]([C:18]2[CH:19]=[CH:20][C:21]3[C:22]4[N:23]=[C:11]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)[CH:12]=[C:13]([C:33]([O:35][CH3:36])=[O:34])[C:14]=4[NH:15][C:16]=3[CH:17]=2)(=[O:26])=[O:25])[CH2:28][CH2:29]1

참가 물질

6

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 86663069methyl 2-bromo-7-(morpholinosulfonyl)-5H-pyrido[3,2-b]indole-4-carboxylate

생성물 1

HCID 66604846methyl 7-(morpholinosulfonyl)-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxylate수율 90%

시약·촉매·용매 1

HCID 167845palladium(II) acetate촉매

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온도
70 °C

실험 절차

A mixture of phenylboronic acid (41.9 mg, 0.343 mmol),methyl 2-bromo-7-(morpholinosulfonyl)-5H-pyrido[3,2-b]indole-4-carboxylate (120 mg, 0.264 mmol), potassium phosphate tribasic (146 mg, 0.687 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (22 mg, 0.053 mmol), and Pd(OAc)2 (5.9 mg, 0.026 mmol) in a microwave vial was flushed with nitrogen. THF (1.3 mL) was added, the vial was capped and the reaction was heated in a 70° C. for 18 hr. It was partitioned between EtOAc and water and the organic phase was separated and washed with brine. It was dried with sodium sulfate and the solvent were removed. The residue was dissolved in DCM and radial chromatography (step gradient elution with DCM containing 0 to 10% EtOAc) afforded methyl 7-(morpholinosulfonyl)-2-phenyl-5H-pyrido[3,2-b]indole-4-carboxylate (107 mg, 0.237 mmol, 90% yield) as a yellow solid. MS (ESI) m/z 450.0 (M−H). 1H NMR (500 MHz, DMSO-d6) d ppm 12.04 (1H, s), 8.58 (1H, d, J=8.24 Hz), 8.47 (1H, s), 8.26 (2H, d, J=7.32 Hz), 8.19 (1H, d, J=1.22 Hz), 7.67 (1H, dd, J=8.24, 1.53 Hz), 7.58 (2H, t, J=7.63 Hz), 7.46-7.52 (1H, m), 4.11 (3H, s), 3.62-3.72 (4H, m), 2.92-3.00 (4H, m).

후처리

  1. customwas flushed with nitrogen
  2. additionTHF (1.3 mL) was added
  3. customthe vial was capped
  4. customIt was partitioned between EtOAc and water
  5. customthe organic phase was separated
  6. washwashed with brine
  7. dry with materialIt was dried with sodium sulfate
  8. customthe solvent were removed
  9. dissolutionThe residue was dissolved in DCM
  10. washradial chromatography (step gradient elution with DCM containing 0 to 10% EtOAc)

출처 및 근거

ORD 기록
ord-bb895f399727479fae69e0514ec9c4cb
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815840B2

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