Hydrochloric Acid → HCID 58532497, compound

HRID 1404591Notes

Reaction equation

HRID 1404591 reaction equation
Br[C:2]1[CH:3]=[C:4]2[N:10]([O:11][CH:12]([C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]([F:21])[C:15]=3[Cl:22])[CH3:13])[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:31]2[CH:32]=[N:33][N:34]([CH:36]3[CH2:41][CH2:40][N:39](C(OC(C)(C)C)=O)[CH2:38][CH2:37]3)[CH:35]=2)O1.Cl>CO>[Cl:22][C:15]1[C:16]([F:21])=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=1[CH:12]([O:11][N:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:31]3[CH:32]=[N:33][N:34]([CH:36]4[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]4)[CH:35]=3)[CH:3]=2)[CH:8]=[CH:9]1)[CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 45480279tert-butyl 4-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylateHCID 674584186-bromo-1-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 58532497HCID 58532497, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The entitled compound was prepared from 6-bromo-1-[1-(2,6-dichloro-3-fluorophenyl)ethoxy]-1H-pyrrolo[3,2-b]pyridine and tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate according to the procedure described in example 4. The resulting compound (BOC protected compound) was dissolved in methanol and was treated with HCl (4.0M solution in dioxane,) at room temperature for 30 min. Solvents were evaporated and the residue was dissolved in DCM and treated with Na2CO3/NaHCO3 and drops of water. The solution was then purified to give the entitled compound.

Workup

  1. customSolvents were evaporated
  2. dissolutionthe residue was dissolved in DCM
  3. additiontreated with Na2CO3/NaHCO3 and drops of water
  4. customThe solution was then purified
  5. customto give the entitled compound

Sources & evidence

ORD record
ord-d54b58944b194dc9a1ef63468f6c49b8
Source dataset
uspto-grants-2014_12
Patent number
US08912330B2

Reaction notes

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