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Sodium Carbonate → Ethyl 3-(3-chloro-5-{5-[6-(methyloxy)-3-biphenylyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate

HRID 423356
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HRID 423356 반응식
Br[C:2]1[CH:3]=[C:4]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]4[C:21](=[CH:22][CH:23]=3)[N:20]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:19]=[C:18]4[Cl:31])[N:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[C:32]1(B(O)O)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[Cl:31][C:18]1[C:17]2[C:21](=[CH:22][CH:23]=[C:15]([C:12]3[N:11]=[C:10]([C:4]4[CH:3]=[C:2]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[C:7]([O:8][CH3:9])=[CH:6][CH:5]=4)[O:14][N:13]=3)[CH:16]=2)[N:20]([CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:19]=1
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6

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HCID 10340Sodium CarbonateHCID 66827Phenylboronic Acid2회HCID 59318425Ethyl 3-(5-{5-[3-bromo-4-(methyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-3-chloro-1H-indol-1-yl)propanoate

생성물 1

HCID 59318433Ethyl 3-(3-chloro-5-{5-[6-(methyloxy)-3-biphenylyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
2회
HCID 80711,2-Dimethoxyethane용매

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온도
90 °C

실험 절차

Ethyl 3-(5-{5-[3-bromo-4-(methyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-3-chloro-1H-indol-1-yl)propanoate (D106) (212 mg, 0.42 mmol), phenyl boronic acid (104 mg, 0.84 mmol), Pd(PPh3)4 (20 mg) and 2N aq. sodium carbonate solution (3 ml, 6 mmol) were suspended in DME (6 ml) and heated at 90° C. for 2 hours. Added phenyl boronic acid (30 mg, 0.24 mmol) and Pd(PPh3)4 (20 mg) and heated at 90° C. for a further 2 hours. Added EtOAc (70 ml) and washed with water (100 ml). Dried over MgSO4 and evaporated off the solvent. The residue was crystallised from ethanol to yield the title compound as 90 mg of light tan solid. MS (ES) C28H2435ClN3O4 requires 501; found 502 (MH+).

후처리

  1. washAdded EtOAc (70 ml) and washed with water (100 ml)
  2. dry with materialDried over MgSO4
  3. customevaporated off the solvent
  4. customThe residue was crystallised from ethanol

출처 및 근거

ORD 기록
ord-7ceec858d6374b69be27125d8a067eac
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08101775B2

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