Dimethylformamide → 3-(4-Amino-3-(3-chloro-4-fluorophenyl)thieno[3,2-c]pyridin-7-yl)benzenesulfonamide

HRID 734313Notes

Reaction equation

HRID 734313 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[C:13]([Cl:18])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5](Br)=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:28]2[CH:29]=[C:30]([S:34]([NH2:37])(=[O:36])=[O:35])[CH:31]=[CH:32][CH:33]=2)O1.C([O-])([O-])=O.[Na+].[Na+].CN(C=O)C>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[C:13]([Cl:18])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([S:34](=[O:36])(=[O:35])[NH2:37])[CH:29]=2)=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 113027877-Bromo-3-(3-chloro-4-fluorophenyl)thieno[3,2-c]pyridin-4-amineHCID 164142303-(Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-sulfonamide

Product 1

HCID 112819303-(4-Amino-3-(3-chloro-4-fluorophenyl)thieno[3,2-c]pyridin-7-yl)benzenesulfonamideYield 20.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

The mixture of 4-amino-7-bromo-3-(3-chloro-4-fluoro-phenyl)thieno[3,2-c]pyridine (40 mg, 0.112 mmol), Pd(PPh3)4 (19 mg, 10 mol %), 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzenesulfonamide (36.8 mg, 0.224 mmol) and 2M Na2CO3 aqueous solution (0.28 ml, 0.56 mmol) in 2 ml of DME was stirred for 14 hours at 80° C. As starting material remained, same amount of reagents described above and DMF (2 ml) were added and stirred for 5 hours at 100° C. The resultant mixture was directly applied to SCX (Varian, 5 g) and eluted with 1N NH3 in CHCl3 and MeOH was collected, and the eluant was concentrated in vacuo. The residue was purified by chromatography on a silica gel column to afford the titled compound (9.8 mg) 1H NMR (400 MHz, DMSO-d6) ppm 8.12 (dd, J=1.8 Hz, 1H), 8.0 s, 1H), 7.91 (ddd, J=1.5, 1.5, 7.6 Hz, 1H), 7.85 (ddd, J=1.4, 1.4, 7.1 Hz, 1H), 7.75 (dd, J=7.8 Hz, 1H), 7.67 (s, 1H), 7.57 (dd, J=9.0 Hz, 1H), 7.51 (ddd, J=2.2, 4.9, 8.5 Hz, 1H), 7.45 (s, 2H), 5.66 (s, 2H). MS: m/z 434 (M+H)+.

Workup

  1. additionwere added
  2. stirringstirred for 5 hours at 100° C
  3. washeluted with 1N NH3 in CHCl3 and MeOH
  4. customwas collected
  5. concentrationthe eluant was concentrated in vacuo
  6. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-1ba32f073e2b4c1bbce14e005cc1d8c3
Source dataset
uspto-grants-2009_09
Patent number
US07592352B2

Reaction notes

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