Sodium Iodide → HCID 52920347, compound

HRID 547854

Reaction equation

HRID 547854 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[C:17]([F:19])[C:16]([F:20])=[CH:15][C:14]=2[O:21][CH3:22])=[CH:9][CH:8]=1.[I-].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].[NH:34]1[CH2:38][CH2:37][CH2:36][C@H:35]1[CH2:39][C:40]([OH:42])=[O:41]>[Cu]I.CS(C)=O>[F:20][C:16]1[C:17]([F:19])=[CH:18][C:13]([C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]3[CH:3]=[C:2]([N:34]4[CH2:38][CH2:37][CH2:36][C@H:35]4[CH2:39][C:40]([OH:42])=[O:41])[CH:25]=[CH:24][CH:23]=3)=[CH:8][CH:9]=2)=[C:14]([O:21][CH3:22])[CH:15]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 2761541Homoproline, (+)-HCID 67153750HCID 67153750, compound

Product 1

HCID 52920347HCID 52920347, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

4′-(3-Bromo-benzyloxy)-4,5-difluoro-2-methoxy-biphenyl (142 mg, 0.35 mmol), copper(I) iodide (40 mg, 0.21 mmol), sodium iodide (105 mg, 0.70 mmol), cesium carbonate (687 mg, 2.1 mmol) and (S)-pyrrolidin-2-yl-acetic acid (106 mg, 0.78 mmol) and DMSO (0.35 ml) were reacted as above to yield 73 mg of {(S)-1-[3-(4′,5′-difluoro-2′-methoxy-biphenyl-4-yloxymethyl)-phenyl]-pyrrolidin-2-yl}-acetic acid as a white solid. LC-MS (ES) calculated for C26H25F2NO4, 453.18; found m/z 454 [M+H]+.

Sources & evidence

ORD record
ord-01e99890f9da43b2bb47289c2ca807ae
Source dataset
uspto-grants-2011_05
Patent number
US07939569B1

Linked notes

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