Triethylamine → 4-(trifluoromethoxy)benzyl 1H-indol-4-ylcarbamate

HRID 887223

반응식

HRID 887223 반응식
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][CH:5]=1.[N:14]([C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[CH:19]=[CH:20][NH:21]2)=[C:15]=[O:16].C(N(CC)CC)C>C1COCC1>[NH:21]1[C:22]2[C:18](=[C:17]([NH:14][C:15](=[O:16])[O:11][CH2:10][C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:12])([F:13])[F:1])=[CH:9][CH:8]=3)[CH:25]=[CH:24][CH:23]=2)[CH:19]=[CH:20]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 1371844-(Trifluoromethoxy)benzenemethanolHCID 220326444-isocyanato-1H-indole

생성물 1

HCID 99751524-(trifluoromethoxy)benzyl 1H-indol-4-ylcarbamate수율 54.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

[4-(Trifluoromethoxy)phenyl]methanol (0.13 g, 0.7 mmol) and the product of Example 80A (0.1 g, 0.63 mmol) in THF (5 mL) were heated at reflux for 16 hours with a catalytic amount of triethylamine. The reaction mixture was concentrated under reduced pressure and the residue was triturated with diethyl ether/hexane to provide the title compound as tan crystals (0.12 g). 1H NMR (300 MHz, DMSO-d6) δ 5.21 (s, 2H), 6.73 (s, 1H), 7.0 (t, 1H), 7.1 (d, 1H), 7.23 (t, 1H), 7.38 (dd, 1H), 7.4 (d, 2H), 7.6 (d, 2H), 9.5 (s, 1H), 11.06 (s, 1H).). Anal. Calcd. for C17H13N2F3O3.0.25H2O: C, 57.55; H, 3.84; N, 7.90. Found: C, 57.42; H, 3.81; N, 7.32.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was triturated with diethyl ether/hexane

출처 및 근거

ORD 기록
ord-d8d27c7a3bee425e80946ed3cfc5a6e9
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247413B2

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