Potassium Phosphate, Tribasic → 1-tert-Butyl 6-methyl 3-phenyl-1H-indole-1,6-dicarboxylate

HRID 409907노트

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HRID 409907 반응식
I[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:3]=1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:22]1([C:2]2[C:10]3[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=3)[N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:3]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 71278271-tert-butyl 6-methyl 3-iodo-1H-indole-1,6-dicarboxylateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

생성물 1

HCID 596260441-tert-Butyl 6-methyl 3-phenyl-1H-indole-1,6-dicarboxylate

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

실험 절차

A mixture of 1-tert-butyl 6-methyl 3-iodo-1H-indole-1,6-dicarboxylate 11a (5.02 mmol, 2.016 g), phenylboronic acid 10b (7.53 mmol, 0.92 g), Pd(OAc)2 (0.402 mmol, 90 mg), Sphos 0.904 mmol, (0.37 g), and K3PO4 (10.1 mmol, 2.13 g) in toluene (10 mL) in sealed reaction vial was stirred at room temperature for 2 min and then heated at 90° C. under N2 for 4 h. The reaction mixture was quenched with EtOAc and water. The organic layer was concentrated and purified by flash column chromatography (silica gel, 8% EtOAc/hexanes). The desired product was collected as a light yellow solid that was washed with small amount of hexanes to obtain 16a as a white solid.

후처리

  1. customin sealed reaction vial
  2. temperatureheated at 90° C. under N2 for 4 h
  3. customThe reaction mixture was quenched with EtOAc and water
  4. concentrationThe organic layer was concentrated
  5. custompurified by flash column chromatography (silica gel, 8% EtOAc/hexanes)
  6. customThe desired product was collected as a light yellow solid
  7. washthat was washed with small amount of hexanes

출처 및 근거

ORD 기록
ord-13c863bdf2e14095b340d4c2a90cdb0e
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759533B2

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