Potassium Carbonate → HCID 71263552, compound

HRID 1424851Notes

Reaction equation

HRID 1424851 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([C:14]2[C:33]([CH:34]3[CH2:36][CH2:35]3)=[CH:32][C:17]3[C:18]([C:28]([NH:30][CH3:31])=[O:29])=[C:19]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)[O:20][C:16]=3[CH:15]=2)[S:10]([CH3:13])(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:44][B:45]1[O:49]C(C)(C)C(C)(C)[O:46]1>CC#N>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([C:14]2[C:33]([CH:34]3[CH2:36][CH2:35]3)=[CH:32][C:17]3[C:18]([C:28](=[O:29])[NH:30][CH3:31])=[C:19]([C:21]4[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=4)[O:20][C:16]=3[CH:15]=2)[S:10]([CH3:13])(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[O:8][CH2:44][B:45]([OH:49])[OH:46]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 109551102-(Bromomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 131732300HCID 131732300, compound

Product 1

HCID 71263552HCID 71263552, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 6-(N-(3-chloro-4-hydroxyphenyl)methylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide (65.0 mg, 0.123 mmol), potassium carbonate (85.0 mg, 0.614 mmol), and 2-(bromomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.109 g, 0.492 mmol) in 4 mL of anhydrous MeCN in a sealed tube was heated to 65° C. with stirring. After 2 hours the mixture was cooled to RT, filtered to remove solids, and the filtrate concentrated to dryness at reduced pressure. The residue was subjected to RP-HPLC purification (C18, MeCN/water/0.1% formic acid) followed by lyophilization from MeCN/water to afford the title compound (43 mg, 60%) as a white powder. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.40-8.47 (m, 1H) 8.20 (s, 1H) 8.05 (s, 2H) 7.97 (dd, J=8.7, 5.5 Hz, 2H) 7.65 (d, J=2.5 Hz, 1H) 7.53 (dd, J=8.9, 2.6 Hz, 1H) 7.40 (t, J=8.8 Hz, 2H) 7.14 (s, 1H) 7.00 (d, J=9.1 Hz, 1H) 3.73 (s, 2H) 3.32 (s, 3H) 2.82 (d, J=4.5 Hz, 3H) 2.20-2.35 (m, 1H) 0.90 (br. s., 3H) 0.45 (br. s., 1H). LCMS (m/z, ES+)=587 (M+H+).

Workup

  1. temperatureAfter 2 hours the mixture was cooled to RT
  2. filtrationfiltered
  3. customto remove solids
  4. concentrationthe filtrate concentrated to dryness at reduced pressure
  5. customThe residue was subjected to RP-HPLC purification (C18, MeCN/water/0.1% formic acid)

Sources & evidence

ORD record
ord-0a105d493cfe4aad9418d05b125b87e3
Source dataset
uspto-grants-2015_01
Patent number
US08927593B2

Reaction notes

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