Potassium Carbonate → HCID 59003341, compound

HRID 2267498Notes

Reaction equation

HRID 2267498 reaction equation
CC(C1CC(C2C3C(=C(C(N)=O)C=C(C4SC=CC=4)C=3)NC=2)CCN1C([O-])=O)(C)C.Br[C:32]1[CH:33]=[C:34]2[C:38](=[C:39]([C:41]([NH2:43])=[O:42])[CH:40]=1)[NH:37][CH:36]=[C:35]2[CH:44]1[CH2:49][CH2:48][N:47]([S:50]([CH2:53][CH2:54][CH2:55][N:56]2[CH2:61][CH2:60][O:59][CH2:58][CH2:57]2)(=[O:52])=[O:51])[CH2:46][CH2:45]1.[OH:62][CH2:63][C:64]1[S:68][C:67](B(O)O)=[CH:66][CH:65]=1.C(=O)([O-])[O-].[K+].[K+]>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>[OH:62][CH2:63][C:64]1[S:68][C:67]([C:32]2[CH:33]=[C:34]3[C:38](=[C:39]([C:41]([NH2:43])=[O:42])[CH:40]=2)[NH:37][CH:36]=[C:35]3[CH:44]2[CH2:45][CH2:46][N:47]([S:50]([CH2:53][CH2:54][CH2:55][N:56]3[CH2:61][CH2:60][O:59][CH2:58][CH2:57]3)(=[O:52])=[O:51])[CH2:48][CH2:49]2)=[CH:66][CH:65]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 43742655-Hydroxymethylthiophene-2-boronic acidHCID 59003290HCID 59003290, compoundHCID 86616130HCID 86616130, compound

Product 1

HCID 59003341HCID 59003341, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared according to the general procedure for intermediate 16. Thus, 5-bromo-3-(1-{[3-(4-morpholinyl)propyl]sulfonyl}-4-piperidinyl)-1H-indole-7-carboxamide (400 mg, 0.78 mmol) in dioxane (3 mL) and water (1 mL), [5-(hydroxymethyl)-2-thienyl]boronic acid (493 mg, 3.12 mmol), Pd(PPh3)4 (90 mg, 10%) and potassium carbonate (861 mg, 6.24 mmol) were reacted to form the desired product which was purified by flash column chromatography (ethyl acetate/hexane, 1/1) to yield the desired product (83 mg, 20%).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-56255c8d23f242528988b4830b817143
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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