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

HRID 340799

반응식

HRID 340799 반응식
[C:1]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=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][CH2:21][CH:22]2[CH2:24][CH:23]2[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:3][CH:2]=1.B(O)(O)[C:37]1[CH:38]=[CH:39][C:40]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)=[CH:41][CH:42]=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:40]1([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:41]=[CH:42][C:37]([C:15]2[C:14]([F:19])=[CH:13][C:12]3[N:8]([CH2:7][C:4]4[CH:3]=[CH:2][C:1]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)=[CH:6][CH:5]=4)[C:9]([O:20][CH2:21][CH:22]4[CH2:24][CH:23]4[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N:10][C:11]=3[C:16]=2[F:17])=[CH:38][CH:39]=1

참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 1512531,1'-Biphenyl-4-yl-boronic acidHCID 67409526Ethyl 2-({[1-(biphenyl-4-ylmethyl)-4,6-difluoro-5-iodo-1H-benzimidazol-2-yl]oxy}methyl)cyclopropanecarboxylate

생성물 1

HCID 71073938Ethyl 2-({[5-(biphenyl-4-yl)-1-(biphenyl-4-ylmethyl)-4,6-difluoro-1H-benzimidazol-2-yl]oxy}methyl)cyclopropanecarboxylate

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
120 °C

실험 절차

A solution of Ethyl 2-({[1-(biphenyl-4-ylmethyl)-4,6-difluoro-5-iodo-1H-benzimidazol-2-yl]oxy}methyl)cyclo-propanecarboxylate (0.0440 g, 0.748 mmol), biphenylboronic acid (0.163 g, 0.823 mmol), and Pd(PPh3)4 (0.035 g, 0.030 mmol) in 7.5 mL of DMF was treated with a 1 M solution of K2CO3 (1.50 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% then 0-20% then 20-30% EtOAc/hexanes) afforded the title compound as a white solid. LCMS: calculated for C39H32F2N2O3 614.68, observed m/e 615.1 (M+H)+ (Rt 2.78/4 min).

후처리

  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%

출처 및 근거

ORD 기록
ord-d6ea4f8aeb654a95b79e587152b52390
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895596B2

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