Dichloromethane → HCID 178509523, compound

HRID 1661651Notes

Reaction equation

HRID 1661651 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([C:18]#[N:19])=[CH:13][CH:12]=2.B(Br)(Br)[Br:21].C(Cl)Cl.C([O-])(O)=O.[Na+]>ClCCCl>[Br:21][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]#[N:19])[CH:15]=2)[NH:10][C:9]=1[C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:3]=1[OH:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 582156342-(4-methoxy-pyridin-3-yl)-1H-indole-5-carbonitrile

Product 1

HCID 178509523HCID 178509523, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A flask is charged with 2-(4-methoxy-pyridin-3-yl)-1H-indole-5-carbonitrile (Example 90, 190 mg, 0.80 mmol) and DCE (8 mL), and 1.0 M BBr3 in DCM (4.8 mL, 4.8 mmol) is added. The mixture is stirred at room temperature overnight. The reaction mixture is poured into saturated aqueous NaHCO3 and extracted with DCM. The aqueous phase is concentrated, acidified with 1M HCl in water and concentrated in vacuo. The residue is purified with an Xbridge C18 eluting with a 1:9 to 9:1 acetonitrile-water gradient to give 3-bromo-2-(4-hydroxy-pyridin-3-yl)-1H-indole-5-carbonitrile. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.40 (d, J=7.1 Hz, 1H), 7.48 (dd, J=8.5, 1.6 Hz, 1H), 7.71 (d, J=8.6 Hz, 1H), 7.81 (dd, J=7.1, 1.3 Hz, 1H), 7.86 (d, J=1.0 Hz, 1H), 8.67 (d, J=1.3 Hz, 1H). HRMS (ESI) m/z 313.9932 [(M+H)+ calcd for C14H9BrN3O: 313.9929].

Workup

  1. additionis added
  2. extractionextracted with DCM
  3. concentrationThe aqueous phase is concentrated
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified with an Xbridge
  6. washC18 eluting with a 1:9 to 9:1 acetonitrile-water gradient

Sources & evidence

ORD record
ord-3df6e470fc3c4706b4d4c87a5db658d3
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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