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Water → HCID 69084584, 화합물

HRID 594760
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HRID 594760 반응식
N1C=CC([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:13]2[N:19]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]4[S:28][CH:29]=[CH:30][N:31]=4)[CH:22]=3)C(=O)[CH2:17][CH2:16][CH2:15][CH2:14]2)=CC=1.[C:33]1(B(O)O)[CH:38]=CC=[CH:35][CH:34]=1.[C:42]([O-:45])([O-])=O.[Na+].[Na+].O.CCO[C:52]([CH3:54])=O>C1COCC1.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:9]1([C:52]2[CH:54]=[CH:35][CH:34]=[CH:33][CH:38]=2)[CH:10]=[CH:11][CH:12]=[CH:7][C:8]=1[CH:13]1[N:19]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]3[S:28][CH:29]=[CH:30][N:31]=3)[CH:22]=2)[C:42](=[O:45])[CH2:17][CH2:16][CH2:15][CH2:14]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 962WaterHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 69084093HCID 69084093, 화합물

생성물 1

HCID 69084584HCID 69084584, 화합물

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

A mixture of 7-(2-bromophenyl)-1-(3-(thiazol-2-yl)benzyl)azepan-2-one (preparation described in example 450; 50 mg; 0.11 mmol), commercially available phenylboronic acid (15 mg; 0.12 mmol), and Pd(PPh3)4 (7 mg; 0.006 mmol) in THF (2 ml), and aq. 2 M Na2CO3 (0.2 ml) was heated to 80° C., under nitrogen, for 24 h. After cooling to rt, water and AcOEt were added. The separated aq. layer was further extracted with AcOEt. The mixed organic layers were washed with brine, dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Subsequent purification by preparative HPLC afforded the target compound. LC-MS (conditions A): tR=0.98 min.; [M+H]+: 439.16 g/mol.

후처리

  1. temperatureAfter cooling to rt
  2. extractionThe separated aq. layer was further extracted with AcOEt
  3. washThe mixed organic layers were washed with brine
  4. dry with materialdried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customSubsequent purification by preparative HPLC
  8. customafforded the target compound

출처 및 근거

ORD 기록
ord-173e25ff9814405a9c7079b0c0ac3a18
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09242970B2

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