Potassium Carbonate → 2-Fluoro-4-(6-nitro-1H-indol-3-yl)-benzonitrile

HRID 2079879

반응식

HRID 2079879 반응식
C1(S([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=3)[C:12]([C:22]3[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[C:24]([F:30])[CH:23]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.C1(S(N2C3C(=CC=C([N+]([O-])=O)C=3)C(Br)=C2)(=O)=O)C=CC=CC=1.FC1C=C(B(O)O)C=CC=1C#N.C([O-])([O-])=O.[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C1COCC1>[F:30][C:24]1[CH:23]=[C:22]([C:12]2[C:13]3[C:18](=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=3)[NH:10][CH:11]=2)[CH:29]=[CH:28][C:25]=1[C:26]#[N:27]

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 2783130(4-Cyano-3-fluorophenyl)boronic acidHCID 574421961-benzenesulfonyl-3-bromo-6-nitro-1H-indoleHCID 671011024-(1-Benzenesulfonyl-6-nitro-1H-indol-3-yl)-2-fluoro-benzonitrile

생성물 1

HCID 574421952-Fluoro-4-(6-nitro-1H-indol-3-yl)-benzonitrile

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

4-(1-Benzenesulfonyl-6-nitro-1H-indol-3-yl)-2-fluoro-benzonitrile from 1-benzenesulfonyl-3-bromo-6-nitro-1H-indole, 7, and 3-fluoro-4-cyanophenylboronic acid using Method AA: Pd2(dba)3, [(t-Bu3)PH]BF4, K2CO3, THF, H2O. Purify by precipitation from EtOAc/hexanes. Remove the benzenesulfonyl protecting group using TBAF and THF as described for 4-(6-nitro-1H-indol-3-yl)-benzonitrile (9) below. LRMS (API ES−)=280.0 (M−1).

후처리

  1. customPurify by precipitation from EtOAc/hexanes
  2. customRemove the benzenesulfonyl protecting group

출처 및 근거

ORD 기록
ord-c55f1a02ecc442089933a62b63cec9f9
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932284B2

연결된 노트

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