Cesium fluoride → (Z)-5-(2-Cyclopentyl-1-hydroxymethyl-vinyl)-thiophene-2-sulfonic acid dimethylaminomethyleneamide

HRID 2103616Notes

Reaction equation

HRID 2103616 reaction equation
[CH:1]1(/[CH:6]=[C:7](/B2OC(C)(C)C(C)(C)O2)\[CH2:8][OH:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:19][N:20]([CH:22]=[N:23][S:24]([C:27]1[S:28][C:29](Br)=[CH:30][CH:31]=1)(=[O:26])=[O:25])[CH3:21].[F-].[Cs+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:21][N:20]([CH:22]=[N:23][S:24]([C:27]1[S:28][C:29](/[C:7](/[CH2:8][OH:9])=[CH:6]\[CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)=[CH:30][CH:31]=1)(=[O:26])=[O:25])[CH3:19]

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 54319951N,N-Dimethyl-N'-(5-bromothiophene-2-sulfonyl)formamidineHCID 67487170(Z)-3-cyclopentyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol

Product 1

HCID 131727584(Z)-5-(2-Cyclopentyl-1-hydroxymethyl-vinyl)-thiophene-2-sulfonic acid dimethylaminomethyleneamide

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

According to method 20b was used (Z)-3-cyclopentyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-prop-2-en-1-ol (678 mg, 2.69 mmol), 5-bromo-thiophene-2-sulfonic acid dimethylaminomethyleneamide (799 mg, 2.69 mmol), caesium fluoride ( 817 mg, 5.38 mmol) and tetrakis-(triphenylphosphin)-palladium(0) (155 mg, 0.135 mmol) to give 538 mg purified product. MS (m/e): 343.0 (M+H).

Workup

  1. customto give 538 mg
  2. custompurified product

Sources & evidence

ORD record
ord-3f2468593725404da546ea12c1e04de0
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

Loading…