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

HRID 2039681

反応式

HRID 2039681 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
65 °C

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-b62db32536984e8b88dc5bf5742e7dd1
出典データセット
uspto-grants-2013_11
特許番号
US08580799B2

関連ノート

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