Potassium Carbonate → HCID 22396766, 화합물

HRID 1370347노트

반응식

HRID 1370347 반응식
[C:1]([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15](Br)[C:14]=3[NH:13][C:12]=2[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CCOC(C)=O.CCCCCCC>O1CCCC1.CN(C)C(=O)C.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>[C:1]([N:9]1[CH2:22][CH2:21][C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:14]=3[NH:13][C:12]=2[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 21899848Ethylacetate heptaneHCID 22396782HCID 22396782, 화합물

생성물 1

HCID 22396766HCID 22396766, 화합물수율 86%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매HCID 31374Dimethylacetamide용매

실험 절차

A mixture of 3-benzoyl-7-bromo-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.517 g, 1.40 mmol), potassium carbonate (0.77 g, 5.60 mmol), phenylboronic acid (0.194 g, 1.54 mmol), tetrakis(triphenylphosphine)palladium (0.16 g, 0.14 mmol) in tetrahydrofuran (7.0 mL) and N,N-dimethylacetamide (7.0 mL) was stirred at room temperature overnight. The mixture was filtered through Celite and the filtrate concentrated in vacuo to give an oil, which was subjected to column chromatography (silica gel, 10-50% EtOAc/heptane) to afford 0.44 g (86%) of the title compound as a solid: mp 198-200° C.; 1H NMR (400 MHz, CDCl3) δ 8.10, 7.67-7.60, 7.55-7.4, 7.47-7.33, 7.18-7.14, 4.04-3.96, 3.72-3.63, 3.20-3.12, 2.93-2.80; IR (drift) 3258, 1602, 1464, 1430, 1327, 1295, 1239, 1185, 930, 761, 749, 740, 711, 703, 696 cm−1; MS (EI) m/z 366 (M+); HRMS (FAB) calcd for C25H22N2O+H: 367.1810, found: 367.1805; Anal. Calcd. for C25H22N2O: C, 81.94; H, 6.05; N, 7.64. Found: C, 81.37; H, 6.12; N, 7.57.

후처리

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate concentrated in vacuo
  3. customto give an oil, which

출처 및 근거

ORD 기록
ord-7eb7dcaa46954daeb410344fe6b394d4
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06583135B2

반응 노트

불러오는 중…