Lithium Chloride → HCID 68313110, compound

HRID 1530676Notes

Reaction equation

HRID 1530676 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[N:8]([CH:9]=[C:10]([C:16]3[N:20]([CH2:21][CH:22]([O:24][CH3:25])[CH3:23])[N:19]=[CH:18][N:17]=3)[N:11]=1)[CH2:7][CH2:6][O:5]2.C([Sn](CCCC)(CCCC)[C:31]([O:33][CH2:34][CH3:35])=[CH2:32])CCC.[Li+].[Cl-].[F-].[K+]>C1COCC1.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>[CH2:34]([O:33][C:31]([C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]1[N:8]([CH:9]=[C:10]([C:16]3[N:20]([CH2:21][CH:22]([O:24][CH3:25])[CH3:23])[N:19]=[CH:18][N:17]=3)[N:11]=1)[CH2:7][CH2:6][O:5]2)=[CH2:32])[CH3:35]

Participants

7

Reactant 4

HCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 68312899HCID 68312899, compound

Product 1

HCID 68313110HCID 68313110, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 12-bromo-4-[1-(2-methoxypropyl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene (290 mg, 0.720 mmol), tributyl(1-ethoxyvinyl)stannane (0.5 mL), Pd(PPh3)4 (27 mg, 0.023 mmol), and LiCl (97 mg, 2.3 mmol) in dry THF (10 mL) was stirred at 70° C. for 48 h under nitrogen atmosphere. KF (40 mL, 0.16 M) was added and the mixture was further stirred at room temperature for 1 h. The solid was filtered off. The filtrate was concentrated to give the crude product, which was purified by reverse phase Combiflash eluting with a 0-50% gradient of CH3CN in 0.3% NH4HCO3 to afford 12-(1-ethoxyethenyl)-4-[1-(2-methoxypropyl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene (195 mg, 66% yield). LCMS (ESI) m/z: 396.3 [M+H+].

Workup

  1. stirringthe mixture was further stirred at room temperature for 1 h
  2. filtrationThe solid was filtered off
  3. concentrationThe filtrate was concentrated
  4. customto give the crude product, which
  5. customwas purified by reverse phase Combiflash
  6. washeluting with a 0-50% gradient of CH3CN in 0.3% NH4HCO3

Sources & evidence

ORD record
ord-bf942fdae62a46fdab5dabde07482fd4
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

Loading…