Hydrochloric Acid → HCID 60026400, compound

HRID 400678Notes

Reaction equation

HRID 400678 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]([CH3:32])([CH3:31])[CH2:12][C:13]([OH:30])([C:26]([F:29])([F:28])[F:27])[CH2:14][C:15]2[NH:23][C:22]3[C:17](=[N:18][C:19]([C:24]#[N:25])=[CH:20][CH:21]=3)[CH:16]=2)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.B.CSC.Cl>C1COCC1.C(OCC)(=O)C>[NH2:25][CH2:24][C:19]1[N:18]=[C:17]2[CH:16]=[C:15]([CH2:14][C:13]([OH:30])([CH2:12][C:11]([C:4]3[C:5]4[O:9][CH2:8][CH2:7][C:6]=4[CH:10]=[C:2]([Cl:1])[CH:3]=3)([CH3:32])[CH3:31])[C:26]([F:29])([F:27])[F:28])[NH:23][C:22]2=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11712374HCID 11712374, compoundHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 60026400HCID 60026400, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-[4-(5-Chloro-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentyl]-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile (100 mg, 0.22 mmol) was dissolved in 3 mL of THF and borane-methyl sulfide (10 M, 0.065 mL, 0.648 mmol) was added. The reaction was heated at reflux for 1 hour and then cooled to room temperature. 1 mL of a 6 N HCl solution was then added. The reaction was heated at reflux overnight. The reaction was cooled to room temperature, diluted with 50 mL of ethyl acetate, and then quenched with saturated sodium carbonate solution until the pH was 12. The organic layer was separated and aqueous layer was extracted with three 50 mL portions of ethyl acetate. The combined organic fractions were dried over sodium sulfate and the solvent was removed in vacuo. The residue was purified by preparative HPLC (polar condition) to give the title compound (49 mg, 49% yield).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 1 hour
  3. temperatureThe reaction was heated
  4. temperatureat reflux overnight
  5. temperatureThe reaction was cooled to room temperature
  6. customquenched with saturated sodium carbonate solution until the pH was 12
  7. customThe organic layer was separated
  8. extractionaqueous layer was extracted with three 50 mL portions of ethyl acetate
  9. dry with materialThe combined organic fractions were dried over sodium sulfate
  10. customthe solvent was removed in vacuo
  11. customThe residue was purified by preparative HPLC (polar condition)

Sources & evidence

ORD record
ord-c70d85bf32434a8d9759f0391fbb4729
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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