Potassium Carbonate → HCID 68328363, compound

HRID 634161Notes

Reaction equation

HRID 634161 reaction equation
[CH3:1][O:2][C:3]1[CH:43]=[CH:42][C:6]([CH2:7][NH:8][C:9]2[S:10][C:11]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[N:19](S(C3C=CC(C)=CC=3)(=O)=O)[CH:18]=[C:17]4B3OC(C)(C)C(C)(C)O3)=[N:12][N:13]=2)=[CH:5][CH:4]=1.Br[C:45]1[N:50]=[C:49]([N:51]2[CH2:56][CH2:55][N:54]3[C:57]([CH3:60])=[N:58][N:59]=[C:53]3[CH2:52]2)[CH:48]=[CH:47][CH:46]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C(Cl)Cl.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>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9]2[S:10][C:11]([C:14]3[CH:15]=[C:16]4[C:20](=[CH:21][CH:22]=3)[NH:19][CH:18]=[C:17]4[C:45]3[CH:46]=[CH:47][CH:48]=[C:49]([N:51]4[CH2:56][CH2:55][N:54]5[C:57]([CH3:60])=[N:58][N:59]=[C:53]5[CH2:52]4)[N:50]=3)=[N:12][N:13]=2)=[CH:42][CH:43]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 68328276HCID 68328276, compoundHCID 86725102HCID 86725102, compound

Product 1

HCID 68328363HCID 68328363, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

A glass microwave reaction vessel was charged with N-(4-methoxybenzyl)-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-thiadiazol-2-amine (90.0 mg, 0.146 mmol) and 7-(6-bromopyridin-2-yl)-3-methyl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine (64.4 mg, 0.219 mmol) in p-dioxane/H2O (3:1, 2.0 mL) followed by potassium carbonate (40.3 mg, 0.292 mmol) and Pd(PPh3)4 (8.43 mg, 7.30 μmol). The reaction was stirred and heated in a microwave at 100° C. for 15 min, then 120° C. for 15 min. The mixture was diluted with DCM and washed with brine, dried, filtered and concentrated to give the crude material. MS (ESI, pos. ion) m/z: 550 (M+1).

Workup

  1. customA glass microwave reaction vessel
  2. washwashed with brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-427952cdcd534b8a8405570dbe059d2c
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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