Trifluoroacetic acid → HCID 71511292, compound

HRID 1055066Notes

Reaction equation

HRID 1055066 reaction equation
[F:1][C:2]1[C:3]([NH:18][C@@H:19]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:20][S:21]([OH:24])(=[O:23])=[O:22])=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[C:14](F)[CH:15]=3)[NH:10][CH:9]=2)=[N:6][CH:7]=1.[Cl:29]C1C=C2C(B3OC(C)(C)C(C)(C)O3)=CN(S(C3C=CC(C)=CC=3)(=O)=O)C2=NC=1.FC1C=C2C(B3OC(C)(C)C(C)(C)O3)=CN(S(C3C=CC(C)=CC=3)(=O)=O)C2=NC=1.C(O)(C(F)(F)F)=O>C(#N)C.O>[Cl:29][C:14]1[CH:15]=[C:16]2[C:8]([C:5]3[N:4]=[C:3]([NH:18][C@@H:19]([C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:20][S:21]([OH:24])(=[O:23])=[O:22])[C:2]([F:1])=[CH:7][N:6]=3)=[CH:9][NH:10][C:11]2=[N:12][CH:13]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 575977475-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 672856905-fluoro-1-((4-methylphenyl)sulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 71511293HCID 71511293, compound

Product 1

HCID 71511292HCID 71511292, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Sulfonic acid, 10, was synthesized in a manner similar to Compound 11, using 5-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine instead of boronate ester, 7a, as the starting material: 1H NMR (400 MHz, MeOD) δ 8.44 (s, 1H), 8.34 (dd, J=9.2, 2.6 Hz, 1H), 8.22 (d, J=5.7 Hz, 1H), 8.13 (s, 1H), 5.16 (d, J=4.1 Hz, 1H), 3.46-3.33 (m, 2H), 1.10 (d, 9H); LC/MS (10-90% ACN/water 5 min with 0.9% TFA, C18) m/z 412.19 (M+H) retention time=1.91 minutes.

Sources & evidence

ORD record
ord-0eca4118ad79426cbe7cc4444ba3e95a
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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