Binap, (A+-)- → HCID 68915125, compound

HRID 870376Notes

Reaction equation

HRID 870376 reaction equation
[F:1][C@@H:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.[C:7]([O:11][C:12](=[O:38])[N:13]([C@H:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([NH:27][S:28]([C:31]3[CH:36]=[CH:35][C:34](Br)=[CH:33][CH:32]=3)(=[O:30])=[O:29])[CH:23]=2)[CH2:18]1)[CH2:14][CH2:15][CH3:16])([CH3:10])([CH3:9])[CH3:8].O(C(C)(C)C)[Na].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:7]([O:11][C:12](=[O:38])[N:13]([C@H:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([NH:27][S:28]([C:31]3[CH:36]=[CH:35][C:34]([N:4]4[CH2:5][CH2:6][C@@H:2]([F:1])[CH2:3]4)=[CH:33][CH:32]=3)(=[O:30])=[O:29])[CH:23]=2)[CH2:18]1)[CH2:14][CH2:15][CH3:16])([CH3:8])([CH3:9])[CH3:10]

Participants

7

Reactant 4

HCID 634876Binap, (A+-)-HCID 27591633-Fluoropyrrolidine2×HCID 68916958HCID 68916958, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 68915125HCID 68915125, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Buchwald coupling reaction using (R)-3-fluoropyrrolidine, Reaction of 0.200 g of [(S)-6-(4-bromo-benzenesulfonylamino)-1,2,3,4-tetrahydronaphthalen-2-yl]-propyl-carbamic acid tert-butyl ester (0.38 mmol), 72 mg of (R)-3-fluoropyrrolidine (0.57 mmol), 51 mg of NaOtC4H9 (1.53 mmol), 39 mg of Pd2(dba)3 (tris(dibenzylideneacetone)dipalladium(0) (0.04 mmol)), 47 mg of BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) (0.08 mmol) in 5 ml tetrahydrofuran at 80° C. for 48 hours yielded 95 mg (47%) of {(S)-6-[4-((R)-3-fluoro-pyrrolidin-1-yl)benzenesulfonylamino]-1,2,3,4-tetrahydro-naphthalen-2-yl}-propyl-carbamic acid tert-butyl ester as a yellow solid.

Workup

  1. customBuchwald coupling reaction

Sources & evidence

ORD record
ord-1708ab016e1245679f41c539321b2958
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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