(3-Fluoropyridin-2-yl)methanol → HCID 67280261, compound

HRID 1693731Notes

Reaction equation

HRID 1693731 reaction equation
[Cl:1][C:2]1[C:7](B2OC(C)(C)C(C)(C)O2)=[CH:6][N:5]=[C:4]2[N:17]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[CH:18]=[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[C:3]=12.[F:35][C:36]1[C:37]([CH2:42][OH:43])=[N:38][CH:39]=[CH:40][CH:41]=1>C1COCC1.C(#N)C.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[Cl:1][C:2]1[C:7]([C:7]2[CH:2]=[C:3]([CH:42]([C:37]3[C:36]([F:35])=[CH:41][CH:40]=[CH:39][N:38]=3)[OH:43])[CH:4]=[N:5][CH:6]=2)=[CH:6][N:5]=[C:4]2[N:17]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:32])[CH3:33])[CH:18]=[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[C:3]=12

Participants

5

Reactant 2

HCID 19703803(3-Fluoropyridin-2-yl)methanolHCID 57537467HCID 57537467, compound

Product 1

HCID 67280261HCID 67280261, compoundYield 176.1%

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 22177404Acetonitrile tetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-chloro-3-(2-fluoro-phenyl)-5-(4,4,5,5-tetramethyl[1,3,2]-dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (100 mg, 0.2 mmol), 5-bromo-pyridin-3-yl)-(3-fluoro-pyridin-2-yl)-methanol (57 mg, 0.2 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (7 mg, 0.01 mmol) in THF/Acetonitrile/saturated NaHCO3 (5 ml/5 ml/5 ml) was stirred at 120° C. in the microwave for 20 minutes. The mixture was allowed to cool down to room temperature and then extracted with ethyl acetate (2×). The combined organic layers were extracted with brine, dried with Na2SO4, decanted, and concentrated to dryness. Silica chromatography of the crude using a gradient of ethyl acetate and hexane afforded {5-[4-chloro-3-(fluoro-phenyl)-1-(2-trimethylsilanyl-ethoxy-methyl)-1H-pyrrolo[2,3-b]pyridine-5-yl]-pyridin-3-yl}-(3-fluoro-pyridin-2-yl)-methanol (102 mg, 88% yield).

Workup

  1. temperatureto cool down to room temperature
  2. extractionextracted with ethyl acetate (2×)
  3. extractionThe combined organic layers were extracted with brine
  4. dry with materialdried with Na2SO4
  5. customdecanted
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e1a48f11b80f4755890607042f33cb20
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

Loading…