Potassium Carbonate → Ethyl 3-{[5-(biphenyl-4-yl)-1-(biphenyl-4-ylmethyl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclopentanecarboxylate

HRID 340791ノート

反応式

HRID 340791 の反応式
[C:1]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:12]3[CH:13]=[C:14]([F:19])[C:15](I)=[C:16]([F:17])[C:11]=3[N:10]=[C:9]2[O:20][CH:21]2[CH2:25][CH2:24][CH:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22]2)=[CH:3][CH:2]=1.B(O)(O)[C:38]1[CH:39]=[CH:40][C:41]([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)=[CH:42][CH:43]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O.O.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>[C:41]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:42]=[CH:43][C:38]([C:15]2[C:14]([F:19])=[CH:13][C:12]3[N:8]([CH2:7][C:4]4[CH:5]=[CH:6][C:1]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[CH:2][CH:3]=4)[C:9]([O:20][CH:21]4[CH2:25][CH2:24][CH:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22]4)=[N:10][C:11]=3[C:16]=2[F:17])=[CH:39][CH:40]=1

参加物

8

反応物 3

HCID 11430Potassium CarbonateHCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 67408440Ethyl 3-{[1-(biphenyl-4-ylmethyl)-4,6-difluoro-5-iodo-1H-benzimidazol-2-yl]oxy}cyclopentanecarboxylate

生成物 1

HCID 67407206Ethyl 3-{[5-(biphenyl-4-yl)-1-(biphenyl-4-ylmethyl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}cyclopentanecarboxylate

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

A solution of ethyl 3-{[1-(biphenyl-4-ylmethyl)-4,6-difluoro-5-iodo-1H-benzimidazol-2-yl]oxy}cyclopentanecarboxylate (0.290 g, 0.481 mmol), biphenylboronic acid (0.105 g, 0.530 mmol), and Pd(PPh3)4 (22 mg, 0.019 mmol) in 4.8 mL of DMF was treated with a 1 M solution of K2CO3 (0.960 mL). The resulting yellow solution was heated at 120° C. for 45 min, and then diluted with EtOAc and H2O. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. Purification of the resulting residue by flash chromatography (0-25% EtOac/hexanes) afforded the desired compound as a white solid. LCMS: calculated for C40H34F2N2O3 628.71, observed m/e 629.1 (M+H)+ (Rt 2.82/4 min).

後処理

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the resulting residue by flash chromatography (0-25% EtOac/hexanes)

出典と根拠

ORDレコード
ord-3886c12536cc447783876bd4beb28eff
出典データセット
uspto-grants-2014_11
特許番号
US08895596B2

反応ノート

読み込み中…