Potassium Phosphate, Tribasic → [3-(1-methyl-1H-indol-2-yl)-pyridin-4-yl]-methanol

HRID 1661630Notes

Reaction equation

HRID 1661630 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1B(O)O.Br[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[CH2:21][OH:22].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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.CN(C=O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[CH2:21][OH:22]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 22733820(1-Methyl-1H-indol-2-yl)boronic acidHCID 46840038(3-Bromopyridin-4-yl)methanol

Product 1

HCID 58215608[3-(1-methyl-1H-indol-2-yl)-pyridin-4-yl]-methanol

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A microwave reactor is charged with 1-methyl-indole-2-boronic acid (1.18 g, 6.78 mmol), (3-bromo-pyridin-4-yl)-methanol (0.850 g, 4.52 mmol), potassium phosphate (1.91 g, 9.04 mmol) and DMF (10 mL). The reactor is evacuated and filled with nitrogen thrice and Pd(PPh3)4 (0.261 g, 0.226 mmol) is added. The reactor is evacuated and filled with nitrogen thrice again. The mixture is heated to 120° C. for 1 h under microwave irradiation, then diluted with ethyl acetate and washed with water thrice. The organic layer is dried over sodium sulfate and concentrated in vacuo to give a residue which is purified by silica gel flash chromatography (dichloromethane-methanol, 19:1) to afford [3-(1-methyl-1H-indol-2-yl)-pyridin-4-yl]-methanol as a white solid. 1H NMR (400 MHz, MeOD) δ ppm 3.58 (s, 3H), 4.57 (s, 2H), 6.54 (s, 1H), 7.14 (t, J=7.5 Hz, 1H), 7.27 (ddd, J=7.6, 1.1 Hz, 1H), 7.46 (d, J=8.3 Hz, 1H), 7.62 (d, J=7.8 Hz, 1H), 7.81 (d, J=5.1 Hz, 1H), 8.49 (s, 1H), 8.67 (d, J=5.1 Hz, 1H). HRMS (ESI) m/z 239.1177 [(M+H)+Calcd for C15H15N2O: 239.1184].

Workup

  1. customThe reactor is evacuated
  2. additionis added
  3. customThe reactor is evacuated
  4. additionfilled with nitrogen thrice again
  5. additiondiluted with ethyl acetate
  6. washwashed with water thrice
  7. dry with materialThe organic layer is dried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give a residue which
  10. customis purified by silica gel flash chromatography (dichloromethane-methanol, 19:1)

Sources & evidence

ORD record
ord-27552aee6f244bf7b55e42abfe95c3c8
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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