Iodine → HCID 118272185, compound

HRID 588140Notes

Reaction equation

HRID 588140 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH:8]=[N:9]O)[C:5]2[C:11]([O:33][CH3:34])=[N:12][N:13]([C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:4]=2[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]2[C:11]([O:33][CH3:34])=[N:12][N:13]([C:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 807IodineHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 137209342HCID 137209342, compound

Product 1

HCID 118272185HCID 118272185, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde oxime (165 mg, 0.352 mmol) was taken up in DCM (6 ml) and triphenylphosphine (92 mg, 0.352 mmol) was added, followed by iodine (89 mg, 0.352 mmol). The resulting mixture was stirred at room temperature overnight. Saturated NaHCO3 was added and the products extracted into EtOAc (×2). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by MPLC (0-25% EtOAc-hexanes) gave 6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbonitrile (42B). 1H NMR (500 MHz, DMSO-d6) δ 7.37 (m, 9H), 7.13 (m, 6H), 5.89 (s, 1H), 3.40 (s, 3H).

Workup

  1. extractionthe products extracted into EtOAc (×2)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by MPLC (0-25% EtOAc-hexanes)

Sources & evidence

ORD record
ord-0b2c6adbeee040d08ed145f2e3a34538
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

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