Tetrahydrofuran → HCID 86706335, compound

HRID 2205948Notes

Reaction equation

HRID 2205948 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[NH:10][C:4]=2[CH:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Na+].C1[CH2:31][O:30][CH2:29][CH2:28]1.BrCCOC>CN(C=O)C.C(OCC)(=O)C.C1(C)C=CC=CC=1>[Br:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[N:10]([CH2:28][CH2:29][O:30][CH3:31])[C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 809722-Bromoethyl methyl etherHCID 2724254Sodium bis(trimethylsilyl)amideHCID 867062766-Bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 86706335HCID 86706335, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine (Preparation 22, 100 mg, 0.36 mmole) was azeotroped with toluene (3 mL) and dissolved in DMF (1 mL). To the solution was added sodium hexamethyldisilazide, 1M in THF (0.4 mL, 0.4 mmole) and the reaction was stirred at room temperature for 20 minutes. Bromoethylmethyl ether (65 uL, 100 mg, 0.8 mmole) was added and the reaction was stirred at room temperature for 18 hours. The reaction was diluted with ethyl acetate (25 mL) and the solution washed with water (3×8 mL) and with brine, dried and evaporated to afford the title compound. 1H-NMR (CDCl3, 500 MHz): δ 3.31 (s, 3H), 3.72 (t, J=5.68 Hz, 2H), 4.01 (s, 3H), 4.28 (t, J=5.68 Hz, 2H), 6.54 (d, J=0.95 Hz, 1H), 7.48 (t, J=0.95 Hz, 1H), 7.71 (s, 1H), 7.74 (d, J=0.95 Hz, 1H), 8.60 (d, J=0.95 Hz, 1H).

Workup

  1. stirringthe reaction was stirred at room temperature for 18 hours
  2. washthe solution washed with water (3×8 mL) and with brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-07951a3809234f79a5934bd47a5a0adc
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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