Sodium Iodide → HCID 52920346, compound

HRID 547853Notes

Reaction equation

[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

Participants

Conditions

Temperature: 100 °C

Procedure

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]+.

Workup

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

Sources & evidence

ORD record: ord-705b9bfed6444c87becea8ec85cfd6d6
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07939569B1

Reaction notes

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