Water → HCID 24967868, compound

HRID 1712961Notes

Reaction equation

HRID 1712961 reaction equation
Br[C:2]1[S:6][C:5]([C:7]([N:9]2[CH:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[OH:20])[CH2:12][C:11]([C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)=[N:10]2)=[O:8])=[CH:4][CH:3]=1.O.CC1(C)C(C)(C)OB([C:36]2[CH:37]=[N:38][NH:39][CH:40]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>CO.CN(C=O)C.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>[NH:38]1[CH:37]=[C:36]([C:2]2[S:6][C:5]([C:7]([N:9]3[CH:13]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[OH:20])[CH2:12][C:11]([C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)=[N:10]3)=[O:8])=[CH:4][CH:3]=2)[CH:40]=[N:39]1

Participants

8

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 59463123HCID 59463123, compound

Product 1

HCID 24967868HCID 24967868, compoundYield 23.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-{1-[(5-bromo-2-thienyl)carbonyl]-3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-5-yl}phenol (0.209 g, 0.488 mmol) in MeOH (1 mL), DMF (1 mL), and water (1 mL) was added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.110 g, 0.567 mmol), tetrakis(triphenylphosphine)palladium(0) (0.032 g, 0.028 mmol) and cesium carbonate (0.318 g, 0.976 mmol). The reaction mixture was subjected to MWI at 100° C. for 15 minutes. A precipitate formed and was filtered and washed with water to give 0.197 grams of crude product as a tan solid. The crude material was purified by column chromatography to give 2-(1-{[5-(1H-pyrazol-4-yl)-2-thienyl]carbonyl}-3-pyridin-3-yl-4,5-dihydro-1H-pyrazol-5-yl)phenol (I-45) (0.048 g, 0.116 mmol) as a white solid. LCMS: (FA) ES+ 416.3, ES 414.3. 1H NMR (400 MHz, d6-DMSO) δ: 9.73-9.82 (bs, 1H), 9.11 (s, 1H), 8.78 (d, 1H), 8.54 (d, 1H), 8.12 (s, 2H), 7.96 (d, 1H), 7.74-7.80 (m, 1H), 7.29 (d, 1H), 7.08 (t, 1H), 6.92 (d, 1H), 6.85 (d, 1H), 6.72 (t, 1H), 5.85 (dd, 1H), 3.90 (dd, 1H), and 3.21 (dd, 1H).

Workup

  1. customA precipitate formed
  2. filtrationwas filtered
  3. washwashed with water
  4. customto give 0.197 grams of crude product as a tan solid
  5. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-fb3a74fd055b4a79a6c3c77712e990d7
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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