Sodium Carbonate → HCID 178472326, compound

HRID 1499271Notes

Reaction equation

HRID 1499271 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:29][CH2:28][C:11]3([CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:13]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:12]3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([CH2:30][O:31][C:32]2[CH:37]=[CH:36][C:35](Br)=[CH:34][CH:33]=2)[N:3]=1.[CH3:39][C:40]1[C:48]2[C:43](=[CH:44][C:45](B3OC(C)(C)C(C)(C)O3)=[CH:46][CH:47]=2)[NH:42][N:41]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:29][CH2:28][C:11]3([CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:13]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:12]3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([CH2:30][O:31][C:32]2[CH:37]=[CH:36][C:35]([C:45]3[CH:44]=[C:43]4[C:48]([C:40]([CH3:39])=[N:41][NH:42]4)=[CH:47][CH:46]=3)=[CH:34][CH:33]=2)[N:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 117942227HCID 117942227, compoundHCID 1784342083-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-indazole

Product 1

HCID 178472326HCID 178472326, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of (S)-2-tert-butyl 3-ethyl 8-(2-amino-6-((4-bromophenoxy)methyl)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate (350 mg, 0.56 mmol), 3-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (285 mg, 1.1 mmol) and Pd(dppf)Cl2 (62 mg, 0.09 mmol) in dioxane (5 mL)/aq. Na2CO3 solution (2.0 M, 5 mL) was heated to 90° C. for 4 h. The reaction was cooled to RT, the solids filtered away, and the solution concentrated in vacuo. Purification on normal phase silica gel (CH2Cl2/MeOH) provided (S)-2-tert-butyl 3-ethyl 8-(2-amino-6-((4-(3-methyl-1H-indazol-6-yl)phenoxy)methyl)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-2,3-dicarboxylate as a brown solid.

Workup

  1. filtrationthe solids filtered away
  2. concentrationthe solution concentrated in vacuo
  3. customPurification on normal phase silica gel (CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-6a83d48a5a8e4b3b8ca74fefeb4e8024
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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