Sodium Carbonate → ({2-Methyl-4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}butyl)oxy]phenyl}oxy)acetic acid

HRID 1391814노트

반응식

HRID 1391814 반응식
Br[C:2]1[N:7]=[C:6]([CH:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]([O:23]CC)=[O:22])=[C:15]([CH3:26])[CH:14]=2)[CH2:9][CH2:10][CH3:11])[CH:5]=[CH:4][CH:3]=1.C1([C:33]2[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[CH:35][C:34]=2B(O)O)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[CH3:26][C:15]1[CH:14]=[C:13]([O:12][CH:8]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([C:34]3[CH:33]=[CH:38][C:37]([C:39]([F:42])([F:41])[F:40])=[CH:36][CH:35]=3)[N:7]=2)[CH2:9][CH2:10][CH3:11])[CH:18]=[CH:17][C:16]=1[O:19][CH2:20][C:21]([OH:23])=[O:22]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 58629817Ethyl [(4-{[1-(6-bromo-2-pyridinyl)butyl]oxy}-2-methylphenyl)oxy]acetateHCID 69207925[2-Phenyl-4-(trifluoromethyl)phenyl]boronic acid

생성물 1

HCID 10366937({2-Methyl-4-[(1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}butyl)oxy]phenyl}oxy)acetic acid수율 21.8%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

A stirred solution of ethyl [(4-{[1-(6-bromo-2-pyridinyl)butyl]oxy}-2-methylphenyl)oxy]acetate (50 mg, 0.12 mmol) in DME (0.5 mL) was treated with phenyl 4-(triflouromethyl)benzeneboronic acid (23 mg, 0.12 mmol) followed by Pd(PPh3)4 (14 mg, 0.01 mmol) and a solution of Na2CO3 (38 mg, 0.36 mmol) in water (0.5 mL), and the resulting mixture was heated at 70° C. for 18 hours under nitrogen. The solvent was then removed under vacuum and the resulting mixture acidified with aqueous HCl (2M) and then partitioned between water and EtOAc, the layers separated and the organic layer reduced to an oil. Purification by mass directed auto-prep HPLC afforded the title compound (12 mg).

후처리

  1. customThe solvent was then removed under vacuum
  2. custompartitioned between water and EtOAc
  3. customthe layers separated
  4. customPurification by mass

출처 및 근거

ORD 기록
ord-e79e50afda424ada8a54314d39c422ce
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07338960B2

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