2-Methyl-2-butene → 6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carboxylic acid

HRID 588133Notes

Reaction equation

HRID 588133 reaction equation
Cl([O-])=O.[Na+].P([O-])(O)(O)=[O:6].[Na+].[Cl:11][C:12]1[N:17]=[C:16]([CH:18]=[O:19])[C:15]2[C:20]([O:42][CH3:43])=[N:21][N:22]([C:23]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:14]=2[CH:13]=1.CC(=CC)C>O.CC(O)(C)C.C1COCC1>[Cl:11][C:12]1[N:17]=[C:16]([C:18]([OH:6])=[O:19])[C:15]2[C:20]([O:42][CH3:43])=[N:21][N:22]([C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:14]=2[CH:13]=1

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 1182719996-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde2×

Product 1

HCID 1182718276-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carboxylic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium chlorite (120 mg, 1.322 mmol) and sodium dihydrogen phosphate (159 mg, 1.322 mmol) were dissolved in water (1.5 ml). A suspension of 6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde (Intermediate 11B, 100 mg, 0.220 mmol) in tBuOH (1.5 ml) and THF (1.5 ml) and 2-methyl-2-butene (233 μl, 2.203 mmol) was then added to the aqueous mixture. The resulting solution was stirred at rt overnight. The reaction contents were concentrated in vacuo, resuspended in water, the solid was filtered, and washed with water. The solids were triturated in MeOH to give 6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carboxylic acid. MS: [M+H]+ m/z 470.

Workup

  1. additionwas then added to the aqueous mixture
  2. customThe reaction contents
  3. concentrationwere concentrated in vacuo
  4. filtrationthe solid was filtered
  5. washwashed with water
  6. customThe solids were triturated in MeOH

Sources & evidence

ORD record
ord-86d17825af594dc1b3748dc67f3a9779
Source dataset
uspto-grants-2016_01
Patent number
US09226922B2

Reaction notes

Loading…