Sodium Carbonate → HCID 58547772, compound

HRID 454938Notes

Reaction equation

HRID 454938 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]1[CH2:15][CH:14]([O:16][C:17]2[C:22](Cl)=[N:21][CH:20]=[CH:19][N:18]=2)[CH2:13]1)=[O:11].[C:24]([Si:28]([CH3:46])([CH3:45])[O:29][CH:30]1[CH2:35][CH2:34][C:33](B2OC(C)(C)C(C)(C)O2)=[CH:32][CH2:31]1)([CH3:27])([CH3:26])[CH3:25].C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1.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.O>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]1[CH2:15][CH:14]([O:16][C:17]2[C:22]([C:33]3[CH2:34][CH2:35][CH:30]([O:29][Si:28]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:45])[CH3:46])[CH2:31][CH:32]=3)=[N:21][CH:20]=[CH:19][N:18]=2)[CH2:13]1)=[O:11]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 218864351,4-Dioxane--water (1/1)HCID 53393368Tert-butyldimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)oxy)silaneHCID 58547720HCID 58547720, compound

Product 1

HCID 58547772HCID 58547772, compoundYield 164%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A glass microwave vessel was charged with (1H-benzo[d]imidazol-2-yl)(3-(3-chloropyrazin-2-yloxy)azetidin-1-yl)methanone (see PREPARATION P23.1; 219 mg, 0.664 mmol), tert-butyldimethyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enyloxy)silane (366 mg, 1.082 mmol, purchased from Small Molecules Inc.), sodium carbonate (211 mg, 1.992 mmol), and dioxane:water (10:1, 15 mL). The solution was purged with N2 for 5 minutes, then palladium tetrakis (153 mg, 0.133 mmol) was added. The reaction mixture was stirred and heated in a Biotage Initiator at 120° C. for 60 minutes. The reaction was poured into water (30 mL) and extracted with EtOAc (2×20 mL). The combined EtOAc layers were eluted through a plug of silica gel. The filtrate was concentrated in vacuo to give crude (1H-benzo[d]imidazol-2-yl)(3-(3-(4-(tert-butyldimethylsilyloxy)cyclohex-1-enyl)pyrazin-2-yloxy)azetidin-1-yl)methanone (550 mg, 164% yield), as a yellow solid. The product was carried forward in the next step without further purification. MS (ESI) m/z 506.3 (MH+).

Workup

  1. customThe solution was purged with N2 for 5 minutes
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe combined EtOAc layers were eluted through a plug of silica gel
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c2121d96bfbd4696ab1120d1b4bbfc58
Source dataset
uspto-grants-2013_07
Patent number
US08497265B2

Reaction notes

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