Potassium Carbonate → 1-(4-Phenoxyphenyl)-3-thiophen-3-yl-imidazo[1,5-a]pyrazin-8-ylamine

HRID 449039Notes

Reaction equation

HRID 449039 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[C:10]([NH2:11])[C:5]2=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)[N:3]=1.[S:25]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26]1.C(=O)([O-])[O-].[K+].[K+].COCCOC.O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[O:18]([C:15]1[CH:16]=[CH:17][C:12]([C:4]2[N:3]=[C:2]([C:27]3[CH:28]=[CH:29][S:25][CH:26]=3)[N:6]3[CH:7]=[CH:8][N:9]=[C:10]([NH2:11])[C:5]=23)=[CH:13][CH:14]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 581760Thiophene-3-boronic acidHCID 18180031Water 1,2-dimethoxyethaneHCID 669155513-Bromo-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazin-8-ylamine

Product 1

HCID 579609461-(4-Phenoxyphenyl)-3-thiophen-3-yl-imidazo[1,5-a]pyrazin-8-ylamine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-bromo-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazin-8-ylamine (20.0 mg, 0.0525 mmol), 3-thiophenylboronic acid (7.38 mg, 0.0577 mmol), Pd(PPh3)4 (10 mg, 0.01 mmol), potassium carbonate (21.8 mg, 0.157 mmol) and DME/Water (5:1) was microwaved at 300 watt, 100° C. for 30 min. The solution was transferred to a 20 mL vial, and 1 mL of DMF was added. The solution was concentrated in vacuo until only DMF remained. The mixture was passed through a syringe filter pad, and prepared for Gilson HPLC separation. The fractions containing the pure product were collected and concentrated in vacuo to afford the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3): δ=6.96 (d, J=5.3 Hz, 1H), 7.07-7.12 (m, 2H), 7.14-7.22 (m, 3H), 7.38-7.43 (m, 2H), 7.55-7.67 (m, 5H), 7.86 (dd, J=3.0, 1.3 Hz, 1H). MS (ES+): m/z 384.94 (100) [MH+]. HPLC: tR=2.58 min (polar—5 min).

Workup

  1. customwas microwaved at 300 watt, 100° C. for 30 min
  2. concentrationThe solution was concentrated in vacuo until only DMF
  3. customThe mixture was passed through a syringe
  4. filtrationfilter pad
  5. customprepared for Gilson HPLC separation
  6. additionThe fractions containing the pure product
  7. customwere collected
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-efe6629819b545ed83bbebad40c72150
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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