2-Fluorophenylboronic acid → HCID 57537614, compound

HRID 1693709Notes

Reaction equation

HRID 1693709 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[N:10][CH:11]=[C:12]([CH:18]=2)[C:13]([N:15]([CH3:17])[CH3:16])=[O:14])=[CH:6][N:5]=[C:4]2[N:19]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH:20]=[C:21](I)[C:3]=12.[F:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1B(O)O>C(#N)C.C1(C)C=CC=CC=1.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[N:10][CH:11]=[C:12]([CH:18]=2)[C:13]([N:15]([CH3:17])[CH3:16])=[O:14])=[CH:6][N:5]=[C:4]2[N:19]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH:20]=[C:21]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=3[F:31])[C:3]=12

Participants

7

Reactant 2

HCID 27343542-Fluorophenylboronic acidHCID 57537599HCID 57537599, compound

Product 1

HCID 57537614HCID 57537614, compound

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
110 °C

Procedure

78 mg (0.14 mmol) of (5-[4-chloro-3-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-nicotinamide, 21 mg (0.15 mmol) of 2-fluoro-phenylboronic acid and 6 mg (7 μmol) of (1,1′-bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichloromethane adduct were dissolved in a mixture of 2.6 mL of acetonitrile, 2.6 mL of toluene and 1.5 mL of a saturated aqueous solution of sodium bicarbonate. The resulting mixture was heated to 110° C. in a closed vial for 22 h. The resulting mixture was diluted with ethyl acetate, dried over sodium sulfate and evaporated. The resulting crude was purified by flash chromatography on silica gel using a gradient of 10% v/v methanol in ethyl acetate and hexanes to afford 56.6 mg (0.10 mmol) of 5-[4-chloro-3-(2-fluoro-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-nicotinamide. 1H-NMR [500 MHz, d6-DMSO] δ: 8.73 (d, 1H), 8.67 (d, 1H), 8.41 (s, 1H), 7.99 (t, 1H), 7.97 (s, 1H), 7.49-7.41 (m, 2H), 7.30-7.25 (m, 2H), 5.74 (s, 2H), 3.62 (t, 2H), 3.01 (s, 3H), 2.97 (s, 3H), 0.86 (t, 2H), −0.06 (s, 9H); MS [MH+] m/z: 525.

Workup

  1. dry with materialdried over sodium sulfate
  2. customevaporated
  3. customThe resulting crude was purified by flash chromatography on silica gel using a gradient of 10% v/v methanol in ethyl acetate and hexanes

Sources & evidence

ORD record
ord-8d45269101ed45c78c1f6178210c3441
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

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