Tributylamine → HCID 86722831, compound

HRID 1778721Notes

Reaction equation

HRID 1778721 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[N:18]=[CH:17][C:16]2[C:19](I)=[N:20][N:21]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)[C:15]=2[CH:14]=1.[CH3:29][C:30]1(C)C(C)(C)OB(C=C)O1.C(N(CCCC)CCCC)CCC>CN(C)C=O.Cl[Pd](Cl)(P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([Cl:12])[C:3]=1[C:13]1[N:18]=[CH:17][C:16]2[C:19]([CH:29]=[CH2:30])=[N:20][N:21]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)[C:15]=2[CH:14]=1

Participants

6

Reactant 3

HCID 7622TributylamineHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 86722830HCID 86722830, compound

Product 1

HCID 86722831HCID 86722831, compound

Reagents, catalysts & solvents 2

HCID 178479802HCID 178479802, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 6-(2,6-dichloro-3,5-dimethoxyphenyl)-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine (100 mg, 0.2 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (44 μL, 0.26 mmol) (Aldrich Cat. No. 633348), tributylamine (54 μL, 0.22 mmol) and dichloro[bis(triphenylphosphoranyl)]palladium (5 mg, 0.007 mmol) in N,N-dimethylformamide (1 mL) in a reaction vial was degassed and sealed. The mixture was stirred at 95° C. for 15 h. After cooling it was equally split into two parts. The material was used in the next step without further purification.

Workup

  1. customsealed
  2. temperatureAfter cooling it
  3. customwas equally split into two parts
  4. customThe material was used in the next step without further purification

Sources & evidence

ORD record
ord-c6760a4896e74180bf540866d575a01b
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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