1-(Bromomethyl)-4-(1,1-dimethylethyl)benzene → 1-(4-(tert-butyl)benzyl)-5-(1H-pyrazol-4-yl)indoline

HRID 63293

반응식

HRID 63293 반응식
[CH:1]([C:4]1[CH:24]=[CH:23][C:7]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([C:18]4[CH:19]=[N:20][NH:21][CH:22]=4)=[CH:15][CH:16]=3)[CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].Br[C:26]1C=C2C(=CC=1)NCC2.BrCC1C=CC(C(C)(C)C)=CC=1.CC1(C)C(C)(C)OB(C2C=NN(C(OC(C)(C)C)=O)C=2)O1>[Pd]>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([C:18]4[CH:22]=[N:21][NH:20][CH:19]=4)=[CH:15][CH:16]=3)[CH2:11][CH2:10]2)=[CH:23][CH:24]=1)([CH3:26])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 34115665-BromoindolineHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 900110621-(4-Isopropylbenzyl)-5-(1H-pyrazol-4-yl)indoline

생성물 1

HCID 900683951-(4-(tert-butyl)benzyl)-5-(1H-pyrazol-4-yl)indoline

시약·촉매·용매 1

HCID 23938Palladium촉매

실험 절차

1-(4-Isopropylbenzyl)-5-(1H-pyrazol-4-yl)indoline, 50 can be prepared by alkylation of 5-bromoindoline, 22 with 1-(bromomethyl)-4-(tert-butyl)benzene using the conditions described in Example 7, part 1 followed by palladium catalyzed coupling of the alkylation product with tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate, 10 followed by hydrolysis using the reaction conditions described in Example 8.

후처리

  1. customfollowed by hydrolysis
  2. customthe reaction conditions

출처 및 근거

ORD 기록
ord-34a0cdaace674f89aedd0d1f89de34d7
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447069B2

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