4-Chloro-5-fluoro-1H-pyrrolo(2,3-b)pyridine → HCID 67277689, compound

HRID 1696236Notes

Reaction equation

HRID 1696236 reaction equation
Cl[C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]2[NH:9][CH:10]=[CH:11][C:3]=12.Cl.[CH3:13][NH:14][C@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]1[CH3:21]>CN1C(=O)N(C)CC1.CCOC(C)=O.O>[F:8][C:7]1[CH:6]=[N:5][C:4]2[NH:9][CH:10]=[CH:11][C:3]=2[C:2]=1[N:14]([CH3:13])[C@H:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]1[CH3:21]

Participants

6

Reactant 2

HCID 497616114-Chloro-5-fluoro-1H-pyrrolo(2,3-b)pyridineHCID 67278419HCID 67278419, compound

Product 1

HCID 67277689HCID 67277689, compoundYield 3.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 66611,3-Dimethyl-2-imidazolidinoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
210 °C

Procedure

A mixture of 4-chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine (100 mg) and (1S,2R)—N,2-dimethylcyclohexanamine hydrochloride (288 mg) in DMI (1 mL) was heated in the microwave reactor (210° C., 2 hours). The reaction mixture was allowed to cool to ambient temperature and diluted with EtOAc (10 mL) and water (10 mL). The aqueous phase was extracted with EtOAc (2×10 mL) and combined organic layers were washed with brine (20 mL), dried over MgSO4, and concentrated. Purification of the crude product by preparative silica gel thin-layer chromatography (chloroform:methanol=10:1) gave 5-fluoro-N-methyl-N-[(1S,2R)-2-methylcyclohexyl]-1H-pyrrolo[2,3-b]pyridin-4-amine (5 mg) as a yellow solid.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionThe aqueous phase was extracted with EtOAc (2×10 mL)
  3. washwere washed with brine (20 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customPurification of the crude product by preparative silica gel thin-layer chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-24037a55e26b4451b27b59330343744d
Source dataset
uspto-grants-2012_04
Patent number
US08163767B2

Reaction notes

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