Water → 4-(6-Amino-5-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridin-3-yl)benzoic acid

HRID 509532ノート

反応式

HRID 509532 の反応式
Br[C:2]1[CH:3]=[C:4]([C:23]2[O:24][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[N:26][N:27]=2)[C:5]([N:8](C(OC(C)(C)C)=O)C(=O)OC(C)(C)C)=[N:6][CH:7]=1.B([C:37]1[CH:45]=[CH:44][C:40]([C:41]([OH:43])=[O:42])=[CH:39][CH:38]=1)(O)O.C([O-])([O-])=O.[Na+].[Na+].O>CC#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([C:37]2[CH:45]=[CH:44][C:40]([C:41]([OH:43])=[O:42])=[CH:39][CH:38]=2)=[CH:3][C:4]=1[C:23]1[O:24][C:25]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[N:26][N:27]=1

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 67481749tert-Butyl N-[5-bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)-2-pyridyl]-N-tert-butoxycarbonyl-carbamate

生成物 1

HCID 674816654-(6-Amino-5-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridin-3-yl)benzoic acid収率 55%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6342Acetonitrile溶媒

反応条件

温度
110 °C

実験手順

A mixture of tert-butyl N-[5-bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)-2-pyridyl]-N-tert-butoxycarbonyl-carbamate (198.7 mg, 0.3841 mmol), 4-boronobenzoic acid (63.74 mg, 0.3841 mmol) and Na2CO3 (81.42 mg, 0.7682 mmol) was suspended in MeCN (3.213 mL)/water (3.213 mL) and degassed (nitrogen/vacuum cycles). The reaction was then treated with tetrakis(triphenylphosphine)palladium(0) (44.39 mg, 0.03841 mmol), degassed again and heated at 110° C. in the microwave for 30 minutes. The reaction was treated with water (0.5 mL) and heated in the microwave at 110° C. for a further 30 minutes. The reaction mixture was washed with DCM, the aqueous phase acidified to pH1 (by addition of 1M HCl), and resulting precipitate filtered off and washed with water to give the product as an orange solid (75 mg, 55% Yield). MS (ES+) 359.14.

後処理

  1. customdegassed (nitrogen/vacuum cycles)
  2. customdegassed again
  3. additionThe reaction was treated with water (0.5 mL)
  4. temperatureheated in the microwave at 110° C. for a further 30 minutes
  5. washThe reaction mixture was washed with DCM
  6. additionthe aqueous phase acidified to pH1 (by addition of 1M HCl)
  7. customresulting precipitate
  8. filtrationfiltered off
  9. washwashed with water

出典と根拠

ORDレコード
ord-4ba81d200c59410bb6508d02fe0a46d5
出典データセット
uspto-grants-2015_08
特許番号
US09096584B2

反応ノート

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