Binap, (A+-)- → HCID 58113978, compound

HRID 1046420Notes

Reaction equation

HRID 1046420 reaction equation
[C:1]([Si:5]([CH3:13])([CH3:12])[O:6][CH2:7][CH2:8][C@@H:9]([NH2:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].[CH3:14][O:15][C:16]([C:18]1[S:19][C:20]([C:24]#[C:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:21][C:22]=1I)=[O:17].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:14][O:15][C:16]([C:18]1[S:19][C:20]([C:24]#[C:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:21][C:22]=1[NH:11][C@@H:9]([CH3:10])[CH2:8][CH2:7][O:6][Si:5]([C:1]([CH3:3])([CH3:2])[CH3:4])([CH3:13])[CH3:12])=[O:17]

Participants

5

Reactant 3

HCID 634876Binap, (A+-)-HCID 581139365-(3,3-Dimethyl-but-1-ynyl)-3-iodo-thiophene-2-carboxylic acid methyl esterHCID 58114107HCID 58114107, compound

Product 1

HCID 58113978HCID 58113978, compound

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

An argon purged flask was charged with 3-(tert-butyl-dimethyl-silanoxy)-1-(S)-methylpropylamine (3.50 g, 17.24 mmol), 5-(3,3-dimethyl-but-1ynyl)-3-iodo-thiophene-2-carboxylic acid methyl ester (3.0 g, 8.62 mmol), Pd(OAc)2 (288 mg, 1.29 mmol), and ±-BINAP 801 mg, 1.29 mmol). Argon degassed toluene (90 mL) was add to the reaction mixture and the reaction was placed in a preheated 120° C. oil bath and stirred for 16 h. The solvent was removed under reduced pressure and taken up in hexanes. 3-[3-(tert-butly-dimethyl-silanoxy)-1-(S)-methyl-propylamino]-5-(3,3-dimethyl-but-1-ynyl)thiophene-2-carboxylic acid methyl ester was isolated by silica gel chromatography (2.87 g, 79%) as a yellow solid.

Workup

  1. customArgon degassed toluene (90 mL)
  2. additionwas add to the reaction mixture
  3. customwas placed in a preheated 120° C.
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-410a6915aa8b431f8e1be0fbf6cf1b72
Source dataset
uspto-grants-2013_10
Patent number
US08569302B2

Reaction notes

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