Water → Ethyl 2-(benzo[d]oxazol-2-yl)nicotinate

HRID 1400236ノート

反応式

HRID 1400236 の反応式
Cl[C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C([Sn](CCCC)(CCCC)[C:18]1[O:19][C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[N:22]=1)CCC.O.CCOC(C)=O>CN(C=O)C.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[O:19]1[C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[N:22]=[C:18]1[C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

参加物

7

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2796614Ethyl chloronicotinateHCID 37665862-(Tributylstannyl)-1,3-benzoxazole

生成物 1

HCID 67540260Ethyl 2-(benzo[d]oxazol-2-yl)nicotinate収率 200.6%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

A mixture of ethyl 2-chloronicotinate (100 mg, 0.539 mmol), 2-(tributylstannyl)benzo[d]oxazole (314 mg, 0.539 mmol) and [1,1′-bis(diphenylphosphino) ferrocene]-dichloropalladium (II) (39.4 mg, 0.054 mmol) in DMF (2 mL) was heated to 110° C. for 1 h by applying microwave radiation to the mixture. The reaction was repeated on the same scale and the thus obtained reaction mixtures obtained were combined. Excess water and EtOAc were added. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water and dried over MgSO4. Purification by flash column chromatography (EtOAc/DCM, gradient: 1-10% DCM) provided the title compound (290 mg, 90%);

後処理

  1. customthe thus obtained reaction mixtures
  2. customobtained
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with EtOAc
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over MgSO4
  7. customPurification by flash column chromatography (EtOAc/DCM, gradient: 1-10% DCM)

出典と根拠

ORDレコード
ord-8b32846cd97c4771ad22c5df00e11639
出典データセット
uspto-grants-2014_12
特許番号
US08906941B2

反応ノート

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