Sodium Carbonate → 6,6-Dimethyl-3-phenyl-1-(pyridin-2-yl)-4,5,6,7-tetrahydroindol-4-one

HRID 1937631노트

반응식

HRID 1937631 반응식
Br[C:2]1[C:10]2[C:9](=[O:11])[CH2:8][C:7]([CH3:13])([CH3:12])[CH2:6][C:5]=2[N:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:3]=1.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][C:7]1([CH3:13])[CH2:6][C:5]2[N:4]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[CH:3]=[C:2]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:10]=2[C:9](=[O:11])[CH2:8]1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 224612763-Bromo-6,6-dimethyl-1-(pyridin-2-yl)-4,5,6,7-tetrahydroindol-4-one

생성물 1

HCID 224612676,6-Dimethyl-3-phenyl-1-(pyridin-2-yl)-4,5,6,7-tetrahydroindol-4-one수율 61.2%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

A solution of 3-bromo-6,6-dimethyl-1-(pyridin-2-yl)-4,5,6,7-tetrahydroindol-4-one (100 mg, 0.31 mmol), phenylboronic acid (153 mg, 1.25 mmol), tetrakis(triphenylphosphine)palladium (50 mg, 0.04 mmol) and Na2CO3 (197 mg, 1.9 mmol) in ethylene glycol dimethyl ether (10 mL) and water (4 mL) was heated at reflux for 8 h. The solvent was evaporated and the residue partitioned between DCM and aqueous K2CO3 (10% (w/v)). The organic layer was separated and the aqueous phase re-extracted with DCM (2×). The combined organic layers were washed with water, dried (MgSO4) and evaporated. The residue was chromatographed on silica gel, eluting with isohexane: EtOAc (9:1), to afford the title compound (60 mg, 61%) as a yellow solid. mp 160-162° C. Found: C, 78.23; H, 6.26; N, 8.57%. Calc. C21H20N2O.0.35(H2O): C, 78.16; H, 6.47; N, 8.68%. 1H NMR (360 MHz, CDCl3) δ 1.13 (6H,s), 2.45 (2H,s), 2.99 (2H,s), 7.17 (1H,s), 7.24-7.38 (5H,m), 7.67 (2H,d, J=7.2 Hz), 7.86 (1H,d of t, J=7.9 and 1.9 Hz), 8.56-8.61 (1H,m). MS (ES+) 317 (M+1).

후처리

  1. temperatureat reflux for 8 h
  2. customThe solvent was evaporated
  3. customthe residue partitioned between DCM and aqueous K2CO3 (10% (w/v))
  4. customThe organic layer was separated
  5. extractionthe aqueous phase re-extracted with DCM (2×)
  6. washThe combined organic layers were washed with water
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was chromatographed on silica gel
  10. washeluting with isohexane: EtOAc (9:1)

출처 및 근거

ORD 기록
ord-ccf5944504de4ab79b9b86aa1d798a3b
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06395766B1

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