1,1'-Carbonyldiimidazole → (5-Bromo-3-pyridinyl)methanol

HRID 1622221Notes

Reaction equation

HRID 1622221 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](O)=[O:8].C1N=CN(C(N2C=NC=C2)=O)C=1.[BH4-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:10]=[C:6]([CH2:7][OH:8])[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 887075-Bromonicotinic acidHCID 4311764Sodium borohydride

Product 1

HCID 2784733(5-Bromo-3-pyridinyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

5-Bromonicotinic acid (3.44 g, 17.0 mmol) is placed in THF (40 mL), combined with CDI (3.00 g, 18.5 mmol) and stirred for 2 h at 50° C. Then while cooling with ice the reaction mixture is poured onto an aqueous NaBH4 solution (600 mg, 15.9 mmol in 100 mL H2O), stirred for 3 d at RT and extracted 7× with DCM. The combined organic phases are dried on Na2SO4, filtered and evaporated down using the rotary evaporator. The (5-bromo-pyridin-3-yl)-methanol thus obtained (HPLC-MS: tRet.=0.21 min; MS (M+H)+=188/190) is further used without any further purification steps.

Workup

  1. temperatureThen while cooling with ice the reaction mixture
  2. stirringstirred for 3 d at RT
  3. extractionextracted 7× with DCM
  4. customThe combined organic phases are dried on Na2SO4
  5. filtrationfiltered
  6. customevaporated down
  7. customthe rotary evaporator

Sources & evidence

ORD record
ord-7ccf20af1f5746fc9ff3a78130860975
Source dataset
uspto-grants-2014_07
Patent number
US08778929B2

Reaction notes

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