Methanol → HCID 57566615、化合物

HRID 1943765ノート

反応式

HRID 1943765 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[C:4]([C:15]2[C:20]([F:21])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:3]=1.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O.[N+:35]([O-])([OH:37])=[O:36].CO>C(O)(C(F)(F)F)=O.O>[Br:1][C:2]1[CH:7]=[C:6]([N+:35]([O-:37])=[O:36])[C:5]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])=[C:4]([C:15]2[C:20]([F:21])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:3]=1

参加物

7

反応物 4

HCID 887MethanolHCID 944Nitric AcidHCID 9845Trifluoroacetic anhydrideHCID 57566613HCID 57566613、化合物

生成物 1

HCID 57566615HCID 57566615、化合物収率 83.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6422Trifluoroacetic acid溶媒2 回

反応条件

温度
0 °C

実験手順

To a suspension of N[4-bromo-2-(3-fluoro-pyridin-2-yl)-phenyl]-2,2-dimethyl-propionamide (6.45 grams, 18.4 mmoles) in TFA (100 mL) and TFAA (25.5 mL, 183.6 mmole), at 0° C., was added a TFA solution (30 mL) of 90% fuming nitric acid (2.46 mL, 55.1 mmoles) over a 45 minute period. The mixture was then stirred at 0° C. for a total of 4 hours. The crude reaction (now homogenous) was poured into ice producing a pasty mass. The mixture was diluted to 500 mL total volume with water, treated with 50 mL of methanol, and vigorously stirred for 12 hours. The resulting solids were filtered, washed with copious amounts of water, then dried in vacuo at 50° C. to afford the title compound (6.1 grams, 82% yield) as a tan powder.

後処理

  1. customThe crude reaction (now homogenous)
  2. additionwas poured into ice producing a pasty mass
  3. stirringvigorously stirred for 12 hours
  4. filtrationThe resulting solids were filtered
  5. washwashed with copious amounts of water
  6. customdried in vacuo at 50° C.

出典と根拠

ORDレコード
ord-9647aa18063e45edb5b7f59150dd8a1b
出典データセット
uspto-grants-2013_03
特許番号
US08394803B2

反応ノート

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