Cesium fluoride → Methyl 7-(2-fluoro-5-methylpyridin-4-yl)-3-(3-(naphthalen-1-yloxy)propyl)-1h-indole-2-carboxylate

HRID 2199739

반응식

HRID 2199739 반응식
[C:1]1([O:11][CH2:12][CH2:13][CH2:14][C:15]2[C:23]3[C:18](=[C:19](B4OC(C)(C)C(C)(C)O4)[CH:20]=[CH:21][CH:22]=3)[NH:17][C:16]=2[C:33]([O:35][CH2:36]C)=[O:34])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[F:38][C:39]1[CH:44]=[C:43](I)[C:42]([CH3:46])=[CH:41][N:40]=1.[F-].[Cs+]>C(COC)OC.CO.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>[F:38][C:39]1[CH:44]=[C:43]([C:19]2[CH:20]=[CH:21][CH:22]=[C:23]3[C:18]=2[NH:17][C:16]([C:33]([O:35][CH3:36])=[O:34])=[C:15]3[CH2:14][CH2:13][CH2:12][O:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[C:42]([CH3:46])=[CH:41][N:40]=1

참가 물질

7

반응물 3

HCID 25953Cesium fluorideHCID 100600522-Fluoro-4-iodo-5-methylpyridineHCID 68940461Ethyl 3-(3-(naphthalen-1-yloxy)propyl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-indole-2-carboxylate

생성물 1

HCID 68939132Methyl 7-(2-fluoro-5-methylpyridin-4-yl)-3-(3-(naphthalen-1-yloxy)propyl)-1h-indole-2-carboxylate

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 887Methanol용매HCID 80711,2-Dimethoxyethane용매

실험 절차

A mixture of EXAMPLE 43A (0.40 g), 2-fluoro-4-iodo-5-methylpyridine (0.209 g), tetrakis(triphenylphosphine)palladium (46 mg) and cesium fluoride (0.365 g) in dimethoxyethane (3 mL) and methanol (1.5 mL) was heated at 120° C. for 20 minutes under microwave conditions (CEM Discovery). After cooling to room temperature, the reaction mixture was loaded onto a silica gel cartridge. The cartridge was dried in vacuum oven for 1 hour and eluted with 1:4 ethyl acetate/hexanes to give the desired product. 1H NMR (500 MHz, DMSO-d6): 11.33 (s, 1H), 8.23-8.25 (m, 1H), 8.17 (s, 1H), 7.86-7.88 (m, 1H), 7.79-7.81 (m, 1H), 7.45-7.56 (m, 3H), 7.39 (t, J=7.93 Hz, 1H), 7.12-7.14 (m, 2H), 7.04 (d, J=2.14 Hz, 1H), 6.91 (d, J=7.32 Hz, 1H), 4.20 (t, J=5.95 Hz, 2H), 3.78 (s, 3H), 3.37 (t, J=7.48 Hz, 2H), 2.20-2.26 (m, 2H), 2.00 (s, 3H).

후처리

  1. customThe cartridge was dried in vacuum oven for 1 hour
  2. washeluted with 1:4 ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-0578b1657f904359b9aad3cefe0edbe3
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359296B2

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