Trifluoroacetic acid → Tert-butyl 5-[5-[3-[bis(tert-butoxycarbonyl)amino]-6-bromopyrazin-2-yl]isoxazol-3-yl]indole-1-carboxylate

HRID 331497

반응식

HRID 331497 반응식
[OH:1][N:2]=[CH:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:8]=[CH:7]2.[Br:20][C:21]1[N:22]=[C:23]([C:42]#[CH:43])[C:24]([N:27]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[N:25][CH:26]=1.C(OI(C1C=CC=CC=1)OC(=O)C)(=O)C.FC(F)(F)C(O)=O>CO>[C:38]([O:37][C:35]([N:27]([C:28]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:34])[C:24]1[C:23]([C:42]2[O:1][N:2]=[C:3]([C:4]3[CH:5]=[C:6]4[C:10](=[CH:11][CH:12]=3)[N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:8]=[CH:7]4)[CH:43]=2)=[N:22][C:21]([Br:20])=[CH:26][N:25]=1)=[O:36])([CH3:41])([CH3:40])[CH3:39]

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 76724Iodobenzene diacetateHCID 58070394tert-butyl N-(5-bromo-3-ethynylpyrazin-2-yl)-N-[(tert-butoxy)carbonyl]carbamateHCID 88996357HCID 88996357, 화합물

생성물 1

HCID 89037198Tert-butyl 5-[5-[3-[bis(tert-butoxycarbonyl)amino]-6-bromopyrazin-2-yl]isoxazol-3-yl]indole-1-carboxylate수율 16.5%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

A solution of tert-butyl 5-((hydroxyimino)methyl)-1H-indole-1-carboxylate (260.3 mg, 1 mmol) in methanol (1 mL) was added slowly to a stirred solution of tert-butyl N-(5-bromo-3-ethynyl-pyrazin-2-yl)-N-tert-butoxycarbonyl-carbamate (438.1 mg, 1.100 mmol) and (diacetoxyiodo)benzene (354.3 mg, 1.100 mmol) in methanol (2 mL) containing trifluoroacetic acid (15 μL, 0.1947 mmol) at ambient temperature. The reaction was stirred at this temperature for 17 hours then concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion, 40 g column) loaded with dichloromethane and eluted with 0 to 50% ethyl acetate/petroleum ether. Product fractions were combined and concentrate in vacuo to give the sub-title product as a white solid (108 mg, 16% Yield). 1H NMR (400.0 MHz, DMSO-d6) δ 1.22 (s, 18H), 1.57 (s, 9H), 6.73 (d, 1H), 7.69 (d, 1H), 7.80 (s, 1H), 7.89 (dd, 1H), 8.11 (d, 1H), 8.23 (d, 1H) and 8.94 (s, 1H) ppm.

후처리

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified by column chromatography (ISCO Companion, 40 g column)
  3. washeluted with 0 to 50% ethyl acetate/petroleum ether
  4. concentrationconcentrate in vacuo

출처 및 근거

ORD 기록
ord-a68360ef282b44fe8b6fd13654043420
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877759B2

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