Sodium Iodide → HCID 52920346, 화합물

HRID 547853

반응식

HRID 547853 반응식
[I-].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].[NH:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]([OH:16])=[O:15].Br[C:18]1[CH:19]=[C:20]([CH:39]=[CH:40][CH:41]=1)[CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[C:33]([F:35])[C:32]([F:36])=[CH:31][C:30]=2[O:37][CH3:38])=[CH:25][CH:24]=1>[Cu]I>[F:36][C:32]1[C:33]([F:35])=[CH:34][C:29]([C:26]2[CH:25]=[CH:24][C:23]([O:22][CH2:21][C:20]3[CH:19]=[C:18]([N:9]4[CH2:13][CH2:12][CH2:11][C@H:10]4[C:14]([OH:16])=[O:15])[CH:41]=[CH:40][CH:39]=3)=[CH:28][CH:27]=2)=[C:30]([O:37][CH3:38])[CH:31]=1

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 145742L-ProlineHCID 671537504'-(3-Bromo-benzyloxy)-4,5-difluoro-2-methoxy-biphenyl

생성물 1

HCID 52920346HCID 52920346, 화합물

시약·촉매·용매 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매

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온도
100 °C

실험 절차

To a vial containing copper(I) iodide (10 mg, 0.050 mmol), sodium iodide (30 mg, 0.2 mmol), cesium carbonate (114 mg, 0.35 mmol) and (S)-pyrrolidine-2-carboxylic acid (14 mg, 0.12 mmol) was added an aliquot of a stock solution of 4′-(3-bromo-benzyloxy)-4,5-difluoro-2-methoxy-biphenyl (1 ml of 0.1M in DMSO). The vial was sealed and heated to 100° C. for 15 hr. The reaction was filtered through Celite and purified by HPLC with increasing concentration of acetonitrile in water with 0.1% trifluoroacetic acid, yielding the product, (S)-1-[3-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-phenyl]-pyrrolidine-2-carboxylic acid as an off white solid (11 mg, 25%). LC-MS (ES) calculated for C25H23F2NO4, 439.16; found m/z 440 [M+H]+.

후처리

  1. customThe vial was sealed
  2. filtrationThe reaction was filtered through Celite
  3. custompurified by HPLC
  4. temperaturewith increasing concentration of acetonitrile in water with 0.1% trifluoroacetic acid

출처 및 근거

ORD 기록
ord-705b9bfed6444c87becea8ec85cfd6d6
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939569B1

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