Tert-Butyl nitrite → 2-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione

HRID 2039681

반응식

HRID 2039681 반응식
N[C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8][N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])[N:6]=1.[Na+].[Br-:21].N(OC(C)(C)C)=O>C(#N)C.O>[Br:21][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8][N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])[N:6]=1

참가 물질

6

반응물 3

HCID 10906Tert-Butyl nitriteHCID 253881Sodium BromideHCID 3410772-[(2-amino-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione

생성물 1

HCID 674242932-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione수율 29.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

반응 조건

온도
65 °C

실험 절차

To a suspension of 2-[(2-amino-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione (4.13 g, 15 mmol), NaBr (3.10 g, 30 mmol) and CuBr (2.15 g, 15 mmol) in acetonitrile (150 mL) at 40° C. under nitrogen atmosphere was added tert-butyl nitrite (2.32 mL, 19.5 mmol) dropwise over 30-40 min. After the addition was complete, heating was maintained towards an internal temp of 60-70° C., and the suspension was stirred at this temperature for 2 h. After cooling down, the mixture was diluted with water, and extracted with ethyl acetate. The combined organic layers (200 mL) were washed with aq HCl (1M, 50 mL), then with brine (50 mL) and dried (MgSO4). After concentration on the rotary evaporator, the residue was purified on silica gel to afford 2-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1H-isoindole-1,3(2H)-dione [1.50 g, yield 28%; HPLC/MS: m/z=339 (M+H); log P(HCOOH)=2.39].

후처리

  1. additionAfter the addition
  2. temperatureheating
  3. temperatureAfter cooling down
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers (200 mL) were washed with aq HCl (1M, 50 mL)
  6. dry with materialwith brine (50 mL) and dried (MgSO4)
  7. concentrationAfter concentration
  8. customon the rotary evaporator
  9. customthe residue was purified on silica gel

출처 및 근거

ORD 기록
ord-b62db32536984e8b88dc5bf5742e7dd1
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580799B2

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