4-Aminobenzyl alcohol → HCID 71014187, compound

HRID 716053Notes

Reaction equation

HRID 716053 reaction equation
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:9][N:8]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:5]2=[N:6][CH:7]=1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][OH:34])=[CH:29][CH:28]=1>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[C:14]([NH:13][C:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([CH2:33][OH:34])=[CH:29][CH:28]=3)[N:3]=2)[N:8]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[CH:9]=1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 2

HCID 693314-Aminobenzyl alcoholHCID 715756452-bromo-N-(tert-butyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Product 1

HCID 71014187HCID 71014187, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a 10 ml seal tube, 2-bromo-N-tert-butyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (0.05 g, 0.000117 mol) and (4-aminophenyl)methanol (0.017 g, 0.00014 mol) was taken in toluene (2.0 ml). The reaction mixture was purged with argon for 15 min at RT after which CS2CO3 (0.189 g, 0.000586 mol) was added and the reaction mixture was further purged for 30 min with argon. BINAP (0.0015 g, 0.0000023 mol) and Pd(OAc)2 (0.0005 g, 0.0000023 mol) were added to reaction mixture and heated to 110° C. for 4 hr. After completion of the reaction, the reaction mixture was filtered through celite bed and washed with ethyl acetate. Filtrate was collected and concentrated to afford crude product which was purified using column purification by eluting the compound with 20-25% ethyl acetate in hexanes to yield 0.05 g of N-tert-butyl-2-(4-(hydroxymethyl)phenyl-amino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide.

Workup

  1. customTo a 10 ml seal tube
  2. additionwas added
  3. customthe reaction mixture was further purged for 30 min with argon
  4. customAfter completion of the reaction
  5. filtrationthe reaction mixture was filtered through celite bed
  6. washwashed with ethyl acetate
  7. customFiltrate was collected
  8. concentrationconcentrated
  9. customto afford crude product which
  10. customwas purified
  11. customcolumn purification
  12. washby eluting the compound with 20-25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-163b63d75d3c47ada5fbeaf3feffa62b
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

Loading…