Potassium Phosphate, Tribasic → HCID 68328772, compound
Reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].CC(N)CC1C=CC=CC=1.OP(O)(O)=O.C(OC([N:31]([CH3:50])[C:32]1[S:36][C:35]([C:37]2[CH:38]=[C:39]3[C:43](=[CH:44][CH:45]=2)[N:42](C([O-])=O)[CH:41]=[C:40]3I)=[N:34][N:33]=1)=O)(C)(C)C.[C:51]1([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[CH:56]=[CH:55][CH:54]=[C:53](B(O)O)[CH:52]=1>CC(O)C.O>[C:51]1([C:60]2[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=2)[CH:56]=[CH:55][CH:54]=[C:53]([C:40]2[C:39]3[C:43](=[CH:44][CH:45]=[C:37]([C:35]4[S:36][C:32]([NH:31][CH3:50])=[N:33][N:34]=4)[CH:38]=3)[NH:42][CH:41]=2)[CH:52]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of potassium phosphate tribasic (80 mg, 0.378 mmol), AmPhos (2.7 mg, 0.00378 mmol), 5-(5-(tert-butoxycarbonyl(methyl)amino)-1,3,4-thiadiazol-2-yl)-3-iodo-1H-indole-1-carboxylate (70 mg, 0.126 mmol), biphenyl-3-ylboronic acid (0.05 g, 0.25 mmol) and 70% IPA/water (1.5 mL) was heated at 80° C. for 3 h. The mixture was concentrated in vacuo and the residue was diluted with 50% DCM/TFA (2 mL). The mixture was stirred at RT for 1 h and the solvent was removed. The residue was purified with RP-HPLC (10-90% MeCN in water with 0.1% TFA) to give 5-(3-(biphenyl-3-yl)-1H-indol-5-yl)-N-methyl-1,3,4-thiadiazol-2-amine (24 mg, 50%). MS (ESI, pos. ion) m/z: 383 (M+1).
Workup
- concentrationThe mixture was concentrated in vacuo
- additionthe residue was diluted with 50% DCM/TFA (2 mL)
- customthe solvent was removed
- customThe residue was purified with RP-HPLC (10-90% MeCN in water with 0.1% TFA)
Sources & evidence
- ORD record
- ord-3d0302bf05404c19821efd20125df98c
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321756B2
Reaction notes
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